Recent Metal-Catalyzed Methods for Thioether Synthesis

Dedicated to Prof. Dr. Štefan Toma on the occasion of his 85^th birthday

Abstract

This review summarizes the more recent methods (since 2015) for the synthesis of thioethers using homogeneous metals as catalysts. The thioether moiety can be found in numerous compounds for pharmaceutical, agricultural, or material applications and it is therefore important to develop new, efficient methods for their synthesis. The recent efforts in this field focus on the use of non-precious metal catalysts, as well as on the development of new bond-forming processes.

1 Introduction

2 Cross-Couplings

3 C–H Activation

4 Hydrothiolation

5 Carbothiolation

6 Miscellaneous

7 Conclusion

Key words

thioethers - sulfides - homogeneous catalysis - coupling - hydrothiolation - C–H activation - decarbonylation

Publication History

Received: 23 June 2022

Accepted after revision: 01 August 2022

Accepted Manuscript online:
01 August 2022

Article published online:
29 August 2022

• References

• 1 Current address: Merck Healthcare KGaA, Frankfurter Straße 250, 64293 Darmstadt, Germany.
• 2 Norgard NB, Hann CL, Dale GL. Clin. Appl. Thromb./Hemostasis 2009; 15: 177
• 3 Bang-Andersen B, Ruhland T, Jørgensen M, Smith G, Frederiksen K, Jensen KG, Zhong H, Nielsen SM, Hogg S, Mørk A, Stensbøl TB. J. Med. Chem. 2011; 54: 3206
• 4 Ilardi EA, Vitaku E, Njardarson JT. J. Med. Chem. 2014; 57: 2832
• 5 Scott KA, Njardarson JT. Top. Curr. Chem. 2018; 376: 5
• 6 Hill HW. Jr, Brady DG. Polym. Eng. Sci. 1976; 16: 831
• 7 Hilton HW, Nomura NS, Yauger WL, Kameda SS. J. Agric. Food. Chem. 1974; 22: 578
• 8 Dörwald FZ. Lead Optimization for Medicinal Chemists . Wiley-VCH; Weinheim: 2012: 100
• 9 McCracken RO, Lipkowitz KB. J. Parasitol. 1990; 76: 180
• 10 The values depicted in Figure 2 were computed using chemaxon.
• 11 Beno BR, Yeung K.-S, Bartberger MD, Pennington LD, Meanwell NA. J. Med. Chem. 2015; 58: 4383
• 12 Honda T, Tajima H, Kaneko Y, Ban M, Inaba T, Takeno Y, Okamoto K, Aono H. Bioorg. Med. Chem. Lett. 2008; 18: 2939
• 13 Tagaki W. In Organic Chemistry of Sulfur . Oae S. Springer US; Boston MA: 1977: 231
• 14 Cheng J.-H, Ramesh C, Kao H.-L, Wang Y.-J, Chan C.-C, Lee C.-F. J. Org. Chem. 2012; 77: 10369
• 15a Leuckart R. J. Prakt. Chem. 1890; 41: 179
• 15b Koziakov D, Majek M, Jacobi von Wangelin A. Org. Biomol. Chem. 2016; 14: 11347
• 16 Sinha AK, Equbal D. Asian J. Org. Chem. 2019; 8: 32
• 17 Massi A, Nanni D. Org. Biomol. Chem. 2012; 10: 3791
• 18 Sundaravelu N, Sangeetha S, Sekar G. Org. Biomol. Chem. 2021; 19: 1459
• 19 Wimmer A, König B. Beistein J. Org. Chem. 2018; 14: 54
• 20a Ghaderi A. Tetrahedron 2016; 72: 4758
• 20b Lee C.-F, Liu Y.-C, Badsara SS. Chem. Asian J. 2014; 9: 706
• 20c Eichman CC, Stambuli JP. Molecules 2011; 16: 590
• 20d Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
• 20e Bichler P, Love JA. In C–X Bond Formation . Vigalok A. Springer; Heidelberg: 2010: 39
• 20f Li J, Yang S, Wu W, Jiang H. Org. Chem. Front. 2020; 7: 1395
• 21 Kosugi M, Shimizu T, Migita T. Chem. Lett. 1978; 7: 13
• 22 Migita T, Shimizu T, Asami Y, Shiobara J.-i, Kato Y, Kosugi M. Bull. Chem. Soc. Jpn. 1980; 53: 1385
• 23 Fernández-Rodríguez MA, Shen Q, Hartwig JF. J. Am. Chem. Soc. 2006; 128: 2180
• 24 Xu J, Liu RY, Yeung CS, Buchwald SL. ACS Catal. 2019; 9: 6461
• 25 Itoh T, Mase T. Org. Lett. 2004; 6: 4587
• 26a Chekal B, Damon D, LaFrance D, Leeman K, Mojica C, Palm A, St Pierre M, Sieser J, Sutherland K, Vaidyanathan R, Van Alsten J, Vanderplas B, Wager C, Weisenburger G, Withbroe G, Yu S. Org. Process Res. Dev. 2015; 19: 1944
• 26b Al-Shuaeeb RA. A, Galvani G, Bernadat G, Brion J.-D, Alami M, Messaoudi S. Org. Biomol. Chem. 2015; 13: 10904
• 27 Scattolin T, Senol E, Yin G, Guo Q, Schoenebeck F. Angew. Chem. Int. Ed. 2018; 57: 12425
• 28 Farmer JL, Pompeo M, Lough AJ, Organ MG. Chem. Eur. J. 2014; 20: 15790
• 29 Jones AC, Nicholson WI, Smallman HR, Browne DL. Org. Lett. 2020; 22: 7433
• 30 Bandaru SS. M, Bhilare S, Cardozo J, Chrysochos N, Schulzke C, Sanghvi YS, Gunturu KC, Kapdi AR. J. Org. Chem. 2019; 84: 8921
• 31 Velasco N, Virumbrales C, Sanz R, Suárez-Pantiga S, Fernández-Rodríguez MA. Org. Lett. 2018; 20: 2848
• 32 Talukder MM, Miller JT, Cue JM. O, Udamulle CM, Bhadran A, Biewer MC, Stefan MC. Organometallics 2021; 40: 83
• 33a Zhao T, Liang F, Cai M, Chen J, Kang C, Wang H, Wu Q. Asian J. Org. Chem. 2020; 9: 214
• 33b Oechsle P, Hou P, Flörke U, Paradies J. Adv. Synth. Catal. 2016; 358: 3770
• 33c Oechsle P, Flörke U, Egold H, Paradies J. Chem. Eur. J. 2016; 22: 18559
• 33d Hou P, Oechsle P, Kuckling D, Paradies J. Macromol. Rapid Commun. 2020; 41: 2000067
• 34 Abidi N, Schmink JR. J. Org. Chem. 2015; 80: 4123
• 35a Chen L, Noory Fajer A, Yessimbekov Z, Kazemi M, Mohammadi M. J. Sulfur Chem. 2019; 40: 451
• 35b Lee C.-F. Phosphorus, Sulfur Silicon Relat. Elem. 2019; 194: 678
• 35c Sambiagio C, Marsden SP, Blacker AJ, McGowan PC. Chem. Soc. Rev. 2014; 43: 3525
• 36a Yamamoto T, Sekine Y. Can. J. Chem. 1984; 62: 1544
• 36b Lindley J. Tetrahedron 1984; 40: 1433
• 37a Kalinin AV, Bower JF, Riebel P, Snieckus V. J. Org. Chem. 1999; 64: 2986
• 37b Palomo C, Oiarbide M, López R, Gómez-Bengoa E. Tetrahedron Lett. 2000; 41: 1283
• 37c Bates CG, Gujadhur RK, Venkataraman D. Org. Lett. 2002; 4: 2803
• 38 Thomas AM, Asha S, Sindhu KS, Anilkumar G. Tetrahedron Lett. 2015; 56: 6560
• 39 Bakare SP, Patil M. New J. Chem. 2022; 46: 6283
• 40 Chen C.-W, Chen Y.-L, Reddy DM, Du K, Li C.-E, Shih B.-H, Xue Y.-J, Lee C.-F. Chem. Eur. J. 2017; 23: 10087
• 41 Nowrouzi N, Abbasi M, Latifi H. Chin. J. Catal. 2016; 37: 1550
• 42 Cao L, Luo S.-H, Wu H.-Q, Chen L.-Q, Jiang K, Hao Z.-F, Wang Z.-Y. Adv. Synth. Catal. 2017; 359: 2961
• 43 Yuan X, Kou Y, Yu L, Zhang Z.-X, Xue W. Org. Chem. Front. 2015; 2: 1604
• 44 Liu Y, Lam LY, Ye J, Blanchard N, Ma C. Adv. Synth. Catal. 2020; 362: 2326
• 45 Chen S, Zhang M, Liao X, Weng Z. J. Org. Chem. 2016; 81: 7993
• 46 Sangeetha S, Muthupandi P, Sekar G. Org. Lett. 2015; 17: 6006
• 47a Sangeetha S, Sekar G. Org. Lett. 2019; 21: 75
• 47b Sundaravelu N, Sekar G. Chem. Commun. 2020; 56: 8826
• 47c Sundaravelu N, Singha T, Nandy A, Sekar G. Chem. Commun. 2021; 57: 4512
• 47d Sangeetha S, Sekar G. Chem. Commun. 2020; 56: 10906
• 47e Sundaravelu N, Sekar G. Org. Lett. 2019; 21: 6648
• 47f Sangeetha S, Sekar G. Org. Lett. 2017; 19: 1670
• 47g Muthupandi P, Sundaravelu N, Sekar G. J. Org. Chem. 2017; 82: 1936
• 48 Zhou L, Chen Z, Li J, Li B. RSC Adv. 2021; 11: 34071
• 49 Cristau HJ, Chabaud B, Chêne A, Christol H. Synthesis 1981; 892
• 50 Kanchana US, Diana EJ, Mathew TV. Asian J. Org. Chem. 2022; 11: e202200038
• 51a Ananikov VP. ACS Catal. 2015; 5: 1964
• 51b Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
• 51c Diccianni JB, Diao T. Trends Chem. 2019; 1: 830
• 52a Wellala NP. N, Guan H. Org. Biomol. Chem. 2015; 13: 10802
• 52b Guo F.-J, Sun J, Xu Z.-Q, Kühn FE, Zang S.-L, Zhou M.-D. Catal. Commun. 2017; 96: 11
• 53 Yu TY, Pang H, Cao Y, Gallou F, Lipshutz BH. Angew. Chem. Int. Ed. 2021; 60: 3708
• 54 Sikari R, Sinha S, Das S, Saha A, Chakraborty G, Mondal R, Paul ND. J. Org. Chem. 2019; 84: 4072
• 55 Yin G, Kalvet I, Englert U, Schoenebeck F. J. Am. Chem. Soc. 2015; 137: 4164
• 56 Zhang C.-P, Vicic DA. J. Am. Chem. Soc. 2012; 134: 183
• 57 Kalvet I, Guo Q, Tizzard GJ, Schoenebeck F. ACS Catal. 2017; 7: 2126
• 58 Jones KD, Power DJ, Bierer D, Gericke KM, Stewart SG. Org. Lett. 2018; 20: 208
• 59 Gehrtz PH, Geiger V, Schmidt T, Srsan L, Fleischer I. Org. Lett. 2019; 21: 50
• 60 Oechsner RM, Wagner JP, Fleischer I. ACS Catal. 2022; 12: 2233
• 61 Martín MT, Marín M, Maya C, Prieto A, Nicasio MC. Chem. Eur. J. 2021; 27: 12320
• 62 Serrano-Becerra JM, Valdés H, Canseco-González D, Gómez-Benítez V, Hernández-Ortega S, Morales-Morales D. Tetrahedron Lett. 2018; 59: 3377
• 63 Liu X, Cao Q, Xu W, Zeng M.-T, Dong Z.-B. Eur. J. Org. Chem. 2017; 2017: 5795
• 64 Zhang J, Wang S, Zhang Y, Feng Z. Asian J. Org. Chem. 2020; 9: 1519
• 65 Correa A, Carril M, Bolm C. Angew. Chem. Int. Ed. 2008; 47: 2880
• 66 Buchwald SL, Bolm C. Angew. Chem. Int. Ed. 2009; 48: 5586
• 67 Sindhu KS, Abi TG, Mathai G, Anilkumar G. Polyhedron 2019; 158: 270
• 68 Hu W, Zhang S. J. Org. Chem. 2015; 80: 6128
• 69 Duan F.-F, Song S.-Q, Xu R.-S. Chem. Commun. 2017; 53: 2737
• 70 Arisawa M, Suzuki T, Ishikawa T, Yamaguchi M. J. Am. Chem. Soc. 2008; 130: 12214
• 71 Wong Y.-C, Jayanth TT, Cheng C.-H. Org. Lett. 2006; 8: 5613
• 72 Liu T.-J, Yi C.-L, Chan C.-C, Lee C.-F. Chem. Asian J. 2013; 8: 1029
• 73 Reddy VP, Swapna K, Kumar AV, Rao KR. J. Org. Chem. 2009; 74: 3189
• 74 Thankachan AP, Sindhu KS, Krishnan KK, Anilkumar G. RSC Adv. 2015; 5: 32675
• 75a Chan DM. T, Monaco KL, Wang R.-P, Winters MP. Tetrahedron Lett. 1998; 39: 2933
• 75b Evans DA, Katz JL, West TR. Tetrahedron Lett. 1998; 39: 2937
• 75c Lam PY. S, Clark CG, Saubern S, Adams J, Winters MP, Chan DM. T, Combs A. Tetrahedron Lett. 1998; 39: 2941
• 76a Luo P.-S, Wang F, Li J.-H, Tang R.-Y, Zhong P. Synthesis 2009; 921
• 76b Xu H.-J, Zhao Y.-Q, Feng T, Feng Y.-S. J. Org. Chem. 2012; 77: 2878
• 77a Barcellos AM, Sacramento M, da Costa GP, Perin G, João Lenardão E, Alves D. Coord. Chem. Rev. 2021; 442: 214012
• 77b Chen J.-Q, Li J.-H, Dong Z.-B. Adv. Synth. Catal. 2020; 362: 3311
• 78a Cheng Y, Liu X, Dong Z.-B. Eur. J. Org. Chem. 2018; 2018: 815
• 78b Liu X, Zhang S.-B, Zhu H, Cheng Y, Peng H.-Y, Dong Z.-B. Eur. J. Org. Chem. 2018; 2018: 4483
• 78c Liu X, Dong Z.-B. J. Org. Chem. 2019; 84: 11524
• 78d Rostami A, Rostami A, Ghaderi A. J. Org. Chem. 2015; 80: 8694
• 78e Wang T.-T, Yang F.-L, Tian S.-K. Adv. Synth. Catal. 2015; 357: 928
• 79 Qiao Z, Ge N, Jiang X. Chem. Commun. 2015; 51: 10295
• 80 Yoshida S, Sugimura Y, Hazama Y, Nishiyama Y, Yano T, Shimizu S, Hosoya T. Chem. Commun. 2015; 51: 16613
• 81 Kanemoto K, Sugimura Y, Shimizu S, Yoshida S, Hosoya T. Chem. Commun. 2017; 53: 10640
• 82a Singh R, Allam BK, Singh N, Kumari K, Singh SK, Singh KN. Adv. Synth. Catal. 2015; 357: 1181
• 82b Bhowmik A, Yadav M, Fernandes RA. Org. Biomol. Chem. 2020; 18: 2447
• 83 Khakyzadeh V, Rostami A, Veisi H, Shirmardi Shaghasemi B, Reimhult E, Luque R, Xia Y, Darvishi S. Org. Biomol. Chem. 2019; 17: 4491
• 84 Wang C, Zhang Z, Tu Y, Li Y, Wu J, Zhao J. J. Org. Chem. 2018; 83: 2389
• 85a Guo L, Rueping M. Acc. Chem. Res. 2018; 51: 1185
• 85b Lu H, Yu T.-Y, Xu P.-F, Wei H. Chem. Rev. 2021; 121: 365
• 85c Liu C, Szostak M. ChemCatChem 2021; 13: 4878
• 86a Shen C, Zhang P, Sun Q, Bai S, Hor TS. A, Liu X. Chem. Soc. Rev. 2015; 44: 291
• 86b Sharma R, Yadav MR. Org. Biomol. Chem. 2021; 19: 5476
• 87 Hirschbeck V, Gehrtz PH, Fleischer I. Chem. Eur. J. 2018; 24: 7092
• 88a Osakada K, Yamamoto T, Yamamoto A. Tetrahedron Lett. 1987; 28: 6321
• 88b Wenkert E, Chianelli D. J. Chem. Soc., Chem. Commun. 1991; 627
• 89 Ichiishi N, Malapit CA, Woźniak Ł, Sanford MS. Org. Lett. 2018; 20: 44
• 90 Lee S.-C, Liao H.-H, Chatupheeraphat A, Rueping M. Chem. Eur. J. 2018; 24: 3608
• 91 Liu C, Szostak M. Chem. Commun. 2018; 54: 2130
• 92 Ishitobi K, Isshiki R, Asahara KK, Lim C, Muto K, Yamaguchi J. Chem. Lett. 2018; 47: 756
• 93a Cao H, Liu X, Bie F, Shi Y, Han Y, Yan P, Szostak M, Liu C. J. Org. Chem. 2021; 86: 10829
• 93b Zhou J.-Y, Tian R, Zhu Y.-M. J. Org. Chem. 2021; 86: 12148
• 93c Cao H, Liu X, Bie F, Shi Y, Han Y, Yan P, Szostak M, Liu C. Org. Chem. Front. 2021; 8: 1587
• 93d Wang S.-F, Li C.-E, Liu Y.-C, Mallikarjuna Reddy D, Sidick Basha R, Park JK, Lee S, Lee C.-F. Asian J. Org. Chem. 2020; 9: 1826
• 93e Han M.-L, Chen J.-J, Xu H, Huang Z.-C, Huang W, Liu Y.-W, Wang X, Liu M, Guo Z.-Q, Dai H.-X. JACS Au 2021; 1: 1877
• 94 Brigham CE, Malapit CA, Lalloo N, Sanford MS. ACS Catal. 2020; 10: 8315
• 95 Zhou J.-Y, Zhu Y.-M. Eur. J. Org. Chem. 2021; 2021: 2452
• 96 Zhou J.-Y, Tao S.-W, Liu R.-Q, Zhu Y.-M. J. Org. Chem. 2019; 84: 11891
• 97 Bie F, Liu X, Cao H, Shi Y, Zhou T, Szostak M, Liu C. Org. Lett. 2021; 23: 8098
• 98 Liu C, Szostak M. Org. Chem. Front. 2021; 8: 4805
• 99 Zheng Z.-J, Jiang C, Shao P.-C, Liu W.-F, Zhao T.-T, Xu P.-F, Wei H. Chem. Commun. 2019; 55: 1907
• 100 Duan Z, Ranjit S, Zhang P, Liu X. Chem. Eur. J. 2009; 15: 3666
• 101 Becht J.-M, Le Drian C. J. Org. Chem. 2011; 76: 6327
• 102 Li M, Hoover JM. Chem. Commun. 2016; 52: 8733
• 103 Green K.-A, Hoover JM. ACS Catal. 2020; 10: 1769
• 104 Liu M, Zhang Z, Chen B, Meng Q, Zhang P, Song J, Han B. Chem. Sci. 2020; 11: 7634
• 105 Liu F, Yi W. Org. Chem. Front. 2018; 5: 428
• 106a Fu Z, Li Z, Xiong Q, Cai H. Eur. J. Org. Chem. 2014; 2014: 7798
• 106b Hu L, Wang D, Chen X, Yu L, Yu Y, Tan Z, Zhu G. Org. Biomol. Chem. 2017; 15: 5674
• 107a Exner B, Bayarmagnai B, Jia F, Goossen LJ. Chem. Eur. J. 2015; 21: 17220
• 107b Exner B, Bayarmagnai B, Matheis C, Goossen LJ. J. Fluorine Chem. 2017; 198: 89
• 108a Wang R, Chen F, Jiang L, Yi W. Adv. Synth. Catal. 2021; 363: 1904
• 108b Wang P, Tang S, Huang P, Lei A. Angew. Chem. Int. Ed. 2017; 56: 3009
• 109 Zhang Y, Sun W, Li C. Synthesis 2022; 54: 281
• 110 Wang Y, Deng L, Wang X, Wu Z, Wang Y, Pan Y. ACS Catal. 2019; 9: 1630
• 111 Liu D, Ma HX, Fang P, Mei TS. Angew. Chem. Int. Ed. 2019; 58: 5033
• 112 Zhu M, Alami M, Messaoudi S. Chem. Commun. 2020; 56: 4464
• 113 Ang NW. J, Ackermann L. Chem. Eur. J. 2021; 27: 4883
• 114 Zhang F, Wang Y, Wang Y, Pan Y. Org. Lett. 2021; 23: 7524
• 115 Kang J.-C, Li Z.-H, Chen C, Dong L.-K, Zhang S.-Y. J. Org. Chem. 2021; 86: 15326
• 116 Wang Y, Zhang F, Wang Y, Pan Y. Eur. J. Org. Chem. 2022; 2022: e202101462
• 117 Savarin C, Srogl J, Liebeskind LS. Org. Lett. 2002; 4: 4309
• 118 Graßl S, Hamze C, Koller TJ, Knochel P. Chem. Eur. J. 2019; 25: 3752
• 119 Dong Z.-B, Balkenhohl M, Tan E, Knochel P. Org. Lett. 2018; 20: 7581
• 120a Chowdhury S, Roy S. Tetrahedron Lett. 1997; 38: 2149
• 120b Taniguchi N. J. Org. Chem. 2004; 69: 6904
• 120c Taniguchi N, Onami T. J. Org. Chem. 2004; 69: 915
• 120d Fukuzawa S.-i, Tanihara D, Kikuchi S. Synlett 2006; 2145
• 120e Gómez-Benítez V, Baldovino-Pantaleón O, Herrera-Álvarez C, Toscano RA, Morales-Morales D. Tetrahedron Lett. 2006; 47: 5059
• 121a Fang Y, Rogge T, Ackermann L, Wang S.-Y, Ji S.-J. Nat. Commun. 2018; 9: 2240
• 121b Li J, Rao W, Wang S.-Y, Ji S.-J. J. Org. Chem. 2019; 84: 11542
• 121c Liu Y, Xing S, Zhang J, Liu W, Xu Y, Zhang Y, Yang K, Yang L, Jiang K, Shao X. Org. Chem. Front. 2022; 9: 1375
• 122 Zhang W, Huang M, Zou Z, Wu Z, Ni S, Kong L, Zheng Y, Wang Y, Pan Y. Chem. Sci. 2021; 12: 2509
• 123 Lian Z, Bhawal BN, Yu P, Morandi B. Science 2017; 356: 1059
• 124 Rivero-Crespo MA, Toupalas G, Morandi B. J. Am. Chem. Soc. 2021; 143: 21331
• 125 Delcaillau T, Bismuto A, Lian Z, Morandi B. Angew. Chem. Int. Ed. 2020; 59: 2110
• 126a Delcaillau T, Boehm P, Morandi B. J. Am. Chem. Soc. 2021; 143: 3723
• 126b Delcaillau T, Morandi B. Chem. Eur. J. 2021; 27: 11823
• 127 Isshiki R, Kurosawa MB, Muto K, Yamaguchi J. J. Am. Chem. Soc. 2021; 143: 10333
• 128a Gensch T, James MJ, Dalton T, Glorius F. Angew. Chem. Int. Ed. 2018; 57: 2296
• 128b Gandeepan P, Muller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
• 128c Grover N, Senge MO. Synthesis 2020; 52: 3295
• 128d Lam NY. S, Wu K, Yu JQ. Angew. Chem. Int. Ed. 2021; 60: 15767
• 129a Liu J, Zheng L. Adv. Synth. Catal. 2019; 361: 1710
• 129b Iwasaki M, Nishihara Y. Dalton Trans. 2016; 45: 15278
• 129c Ma W, Kaplaneris N, Fang X, Gu L, Mei R, Ackermann L. Org. Chem. Front. 2020; 7: 1022
• 130 Yang Y, Hou W, Qin L, Du J, Feng H, Zhou B, Li Y. Chem. Eur. J. 2014; 20: 416
• 131 Rui X, Zhu Y, Dai R, Huang C, Wang C, Si D, Wang X, Zhang X, Wen H, Li W, Liu J. Asian J. Org. Chem. 2021; 10: 793
• 132 Shi G, Khan R, Zhang X, Yang Y, Zhan Y, Li J, Luo Y, Fan B. Asian J. Org. Chem. 2020; 9: 788
• 133 Yang S, Feng B, Yang Y. J. Org. Chem. 2017; 82: 12430
• 134 Wen J, Wu A, Wang M, Zhu J. J. Org. Chem. 2015; 80: 10457
• 135 Maity S, Karmakar U, Samanta R. Chem. Commun. 2017; 53: 12197
• 136 Lin J, Hu L, Chen C, Feng H, Yu Y, Yang Y, Zhou B. Org. Lett. 2021; 23: 1194
• 137 Liu C, Fang Y, Wang S.-Y, Ji S.-J. Org. Lett. 2018; 20: 6112
• 138 Liu C, Fang Y, Wang S.-Y, Ji S.-J. ACS Catal. 2019; 9: 8910
• 139 Sumit, Chandra D, Thakur A, Dhiman AK, Sharma U. J. Org. Chem. 2021; 86: 13754
• 140a Iwasaki M, Iyanaga M, Tsuchiya Y, Nishimura Y, Li W, Li Z, Nishihara Y. Chem. Eur. J. 2014; 20: 2459
• 140b Xu C, Shen Q. Org. Lett. 2014; 16: 2046
• 141 Qiu R, Reddy VP, Iwasaki T, Kambe N. J. Org. Chem. 2015; 80: 367
• 142 Chaitanya M, Anbarasan P. Org. Lett. 2018; 20: 3362
• 143 Zhang X.-S, Li G, Zhang X.-G, Zhang X.-H. Tetrahedron 2015; 71: 5458
• 144 Tzouras NV, Stamatopoulos IK, Papastavrou AT, Liori AA, Vougioukalakis GC. Coord. Chem. Rev. 2017; 343: 25
• 145 Gao F, Zhu W, Zhang D, Li S, Wang J, Liu H. J. Org. Chem. 2016; 81: 9122
• 146 Zhu J, Chen Y, Lin F, Wang B, Chen Z, Liu L. Org. Biomol. Chem. 2015; 13: 3711
• 147 Yan S.-Y, Liu Y.-J, Liu B, Liu Y.-H, Shi B.-F. Chem. Commun. 2015; 51: 4069
• 148a Lin C, Li D, Wang B, Yao J, Zhang Y. Org. Lett. 2015; 17: 1328
• 148b Lin C, Yu W, Yao J, Wang B, Liu Z, Zhang Y. Org. Lett. 2015; 17: 1340
• 148c Ye X, Petersen JL, Shi X. Chem. Commun. 2015; 51: 7863
• 149 Müller T, Ackermann L. Chem. Eur. J. 2016; 22: 14151
• 150a Chu L, Yue X, Qing F.-L. Org. Lett. 2010; 12: 1644
• 150b Chen C, Xu XH, Yang B, Qing FL. Org. Lett. 2014; 16: 3372
• 150c Zhang X, Zeng W, Yang Y, Huang H, Liang Y. Org. Lett. 2014; 16: 876
• 151 Xiong Y.-S, Yu Y, Weng J, Lu G. Org. Chem. Front. 2018; 5: 982
• 152 Yang L.-F, Liu C.-G, Xu X.-P, Ji S.-J. Org. Biomol. Chem. 2016; 14: 2993
• 153 Tian L.-L, Lu S, Zhang Z.-H, Huang E.-L, Yan H.-T, Zhu X, Hao X.-Q, Song M.-P. J. Org. Chem. 2019; 84: 5213
• 154 Le Bescont J, Breton-Patient C, Piguel S. Eur. J. Org. Chem. 2020; 2020: 2101
• 155 Moselage M, Li J, Ackermann L. ACS Catal. 2016; 6: 498
• 156a Li M, Wang JJ. Org. Lett. 2018; 20: 6490
• 156b Hu L, Chen X, Yu L, Yu Y, Tan Z, Zhu G, Gui Q. Org. Chem. Front. 2018; 5: 216
• 157 Gensch T, Klauck FJ. R, Glorius F. Angew. Chem. Int. Ed. 2016; 55: 11287
• 158 Panova YS, Kashin AS, Vorobev MG, Degtyareva ES, Ananikov VP. ACS Catal. 2016; 6: 3637
• 159 Liu X.-G, Li Q, Wang H. Adv. Synth. Catal. 2017; 359: 1942
• 160 López-Resano S, Martínez de Salinas S, Garcés-Pineda FA, Moneo-Corcuera A, Galán-Mascarós JR, Maseras F, Pérez-Temprano MH. Angew. Chem. Int. Ed. 2021; 60: 11217
• 161 Ghorai J, Kesavan A, Anbarasan P. Chem. Commun. 2021; 57: 10544
• 162 Qin L, Wu H.-b, Weng L, Shen Q, Chen H. SynOpen 2020; 4: 17
• 163 Hsu W.-C, Li C.-E, Lee C.-F. Asian J. Org. Chem. 2017; 6: 1667
• 164 Xiao F, Yuan S, Wang D, Liu S, Huang H, Deng G.-J. Adv. Synth. Catal. 2019; 361: 3331
• 165a Ma W, Weng Z, Rogge T, Gu L, Lin J, Peng A, Luo X, Gou X, Ackermann L. Adv. Synth. Catal. 2018; 360: 704
• 165b Bag R, Sarkar T, Kumar SV, Talukdar K, Punniyamurthy T. J. Chem. Sci. 2019; 131: 115
• 166a Posner T. Ber. Dtsch. Chem. Ges. 1905; 38: 646
• 166b Bader H, Cross LC, Heilbron I, Jones ER. H. J. Chem. Soc. 1949; 619
• 167a Crossley SW. M, Obradors C, Martinez RM, Shenvi RA. Chem. Rev. 2016; 116: 8912
• 167b Castarlenas R, Di Giuseppe A, Perez-Torrente JJ, Oro LA. Angew. Chem. Int. Ed. 2013; 52: 211
• 167c Beletskaya IP, Nájera C, Yus M. Russ. Chem. Rev. 2021; 90: 70
• 168a Cao C, Fraser LR, Love JA. J. Am. Chem. Soc. 2005; 127: 17614
• 168b Di Giuseppe A, Castarlenas R, Pérez-Torrente JJ, Crucianelli M, Polo V, Sancho R, Lahoz FJ, Oro LA. J. Am. Chem. Soc. 2012; 134: 8171
• 168c Ogawa A, Ikeda T, Kimura K, Hirao T. J. Am. Chem. Soc. 1999; 121: 5108
• 169 Kiemele ER, Wathier M, Bichler P, Love JA. Org. Lett. 2016; 18: 492
• 170 Strydom I, Guisado-Barrios G, Fernandez I, Liles DC, Peris E, Bezuidenhout DI. Chem. Eur. J. 2017; 23: 1393
• 171 Tolley LC, Fernández I, Bezuidenhout DI, Guisado-Barrios G. Catal. Sci. Technol. 2021; 11: 516
• 172 Kleinhans G, Guisado-Barrios G, Liles DC, Bertrand G, Bezuidenhout DI. Chem. Commun. 2016; 52: 3504
• 173 Pritzius AB, Breit B. Angew. Chem. Int. Ed. 2015; 54: 3121
• 174 Pritzius AB, Breit B. Angew. Chem. Int. Ed. 2015; 54: 15818
• 175 Kennemur JL, Kortman GD, Hull KL. J. Am. Chem. Soc. 2016; 138: 11914
• 176 Han L, Li Y, Liu T. Dalton Trans. 2018; 47: 150
• 177 Yang X.-H, Davison RT, Dong VM. J. Am. Chem. Soc. 2018; 140: 10443
• 178 Yang X.-H, Davison RT, Nie S.-Z, Cruz FA, McGinnis TM, Dong VM. J. Am. Chem. Soc. 2019; 141: 3006
• 179 Wen X, Zhou X, Li W, Du C, Ke Z, Zhao C. ACS Catal. 2021; 11: 7659
• 180 Nie S, Lu A, Kuker EL, Dong VM. J. Am. Chem. Soc. 2021; 143: 6176
• 181a Corma A, González-Arellano C, Iglesias M, Sánchez F. Appl. Catal., A 2010; 375: 49
• 181b Biswas S, Samec JS. M. Chem. Commun. 2012; 48: 6586
• 181c Mudd RJ, Young PC, Jordan-Hore JA, Rosair GM, Lee A.-L. J. Org. Chem. 2012; 77: 7633
• 181d Biswas S, Dahlstrand C, Watile RA, Kalek M, Himo F, Samec JS. M. Chem. Eur. J. 2013; 19: 17939
• 182 Martínez-Lara F, Suárez A, Velasco N, Suárez-Pantiga S, Sanz R. Adv. Synth. Catal. 2022; 364: 132
• 183 Tamai T, Fujiwara K, Higashimae S, Nomoto A, Ogawa A. Org. Lett. 2016; 18: 2114
• 184 Kristensen SK, Laursen SL. R, Taarning E, Skrydstrup T. Angew. Chem. Int. Ed. 2018; 57: 13887
• 185 Kuniyasu H, Ogawa A, Sato K, Ryu I, Kambe N, Sonoda N. J. Am. Chem. Soc. 1992; 114: 5902
• 186a Ananikov VP, Orlov NV, Zalesskiy SS, Beletskaya IP, Khrustalev VN, Morokuma K, Musaev DG. J. Am. Chem. Soc. 2012; 134: 6637
• 186b Gerber R, Frech CM. Chem. Eur. J. 2012; 18: 8901
• 186c Degtyareva ES, Burykina JV, Fakhrutdinov AN, Gordeev EG, Khrustalev VN, Ananikov VP. ACS Catal. 2015; 5: 7208
• 187 Sahharova LT, Gordeev EG, Eremin DB, Ananikov VP. ACS Catal. 2020; 10: 9872
• 188 Lopes AB, Choury M, Wagner P, Gulea M. Org. Lett. 2019; 21: 5943
• 189 Ogawa A, Kawakami J.-i, Sonoda N, Hirao T. J. Org. Chem. 1996; 61: 4161
• 190 Tamai T, Ogawa A. J. Org. Chem. 2014; 79: 5028
• 191 Kathe PM, Fleischer I. Org. Lett. 2019; 21: 2213
• 192 Zhang Y, Xu X, Zhu S. Nat. Commun. 2019; 10: 1752
• 193a Ananikov VP, Orlov NV, Beletskaya IP. Organometallics 2006; 25: 1970
• 193b Malyshev DA, Scott NM, Marion N, Stevens ED, Ananikov VP, Beletskaya IP, Nolan SP. Organometallics 2006; 25: 4462
• 193c Ananikov VP, Gayduk KA, Orlov NV, Beletskaya IP, Khrustalev VN, Antipin MY. Chem. Eur. J. 2010; 16: 2063
• 194 Ren S, Xue B, Zheng T, Wang Y, Sun H, Li X, Fuhr O, Fenske D. Appl. Organomet. Chem. 2020; 34: e5291
• 195a Nurhanna Riduan S, Ying JY, Zhang Y. Org. Lett. 2012; 14: 1780
• 195b Trostyanskaya IG, Beletskaya IP. Synlett 2012; 535
• 195c Watile RA, Biswas S, Samec JS. M. Green Chem. 2013; 15: 3176
• 196 Wang G, Khan R, Liu H, Shen G, Yang F, Chen J, Zhou Y, Fan B. Organometallics 2020; 39: 2037
• 197a Sonehara T, Murakami S, Yamazaki S, Kawatsura M. Org. Lett. 2017; 19: 4299
• 197b Yang T, Lu L, Shen Q. Chem. Commun. 2015; 51: 5479
• 197c Cabrero-Antonino JR, Leyva-Pérez A, Corma A. Adv. Synth. Catal. 2012; 354: 678
• 198 Taniguchi N. J. Org. Chem. 2020; 85: 6528
• 199a Kucinski K, Pawluc P, Marciniec B, Hreczycho G. Chem. Eur. J. 2015; 21: 4940
• 199b Kuciński K, Pawluć P, Hreczycho G. Adv. Synth. Catal. 2015; 357: 3936
• 200a Lou J, Wang Q, Wu P, Wang H, Zhou Y.-G, Yu Z. Chem. Soc. Rev. 2020; 49: 4307
• 200b Wang L, He W, Yu Z. Chem. Soc. Rev. 2013; 42: 599
• 201a Hooper JF, Chaplin AB, González-Rodríguez C, Thompson AL, Weller AS, Willis MC. J. Am. Chem. Soc. 2012; 134: 2906
• 201b Arisawa M, Igarashi Y, Tagami Y, Yamaguchi M, Kabuto C. Tetrahedron Lett. 2011; 52: 920
• 201c Arambasic M, Hooper JF, Willis MC. Org. Lett. 2013; 15: 5162
• 202a Iwasaki M, Fujino D, Wada T, Kondoh A, Yorimitsu H, Oshima K. Chem. Asian J. 2011; 6: 3190
• 202b Hua R, Takeda H, Onozawa S.-y, Abe Y, Tanaka M. J. Am. Chem. Soc. 2001; 123: 2899
• 202c Minami Y, Kuniyasu H, Sanagawa A, Kambe N. Org. Lett. 2010; 12: 3744
• 202d Minami Y, Kuniyasu H, Miyafuji K, Kambe N. Chem. Commun. 2009; 3080
• 202e Toyofuku M, Fujiwara S.-i, Shin-ike T, Kuniyasu H, Kambe N. J. Am. Chem. Soc. 2005; 127: 9706
• 203a Sugoh K, Kuniyasu H, Sugae T, Ohtaka A, Takai Y, Tanaka A, Machino C, Kambe N, Kurosawa H. J. Am. Chem. Soc. 2001; 123: 5108
• 203b Toyofuku M, Fujiwara S.-i, Shin-ike T, Kuniyasu H, Kambe N. J. Am. Chem. Soc. 2008; 130: 10504
• 204 Ren P, Pike SD, Pernik I, Weller AS, Willis MC. Organometallics 2015; 34: 711
• 205 Shibata T, Mitake A, Akiyama Y, Kanyiva KS. Chem. Commun. 2017; 53: 9016
• 206 Iwasaki M, Topolovčan N, Hu H, Nishimura Y, Gagnot G, Na nakorn R, Yuvacharaskul R, Nakajima K, Nishihara Y. Org. Lett. 2016; 18: 1642
• 207 Uno D, Nogi K, Yorimitsu H. Org. Lett. 2019; 21: 8295
• 208 Wu J, Xu W.-H, Lu H, Xu P.-F. Adv. Synth. Catal. 2021; 363: 3013
• 209 Hosoya Y, Kobayashi I, Mizoguchi K, Nakada M. Org. Lett. 2019; 21: 8280
• 210 Kim H, Jang J, Shin S. J. Am. Chem. Soc. 2020; 142: 20788
• 211 Wang J, Zhang S, Xu C, Wojtas L, Akhmedov NG, Chen H, Shi X. Angew. Chem. Int. Ed. 2018; 57: 6915
• 212a Inami T, Kurahashi T, Matsubara S. Chem. Commun. 2011; 47: 9711
• 212b Inami T, Baba Y, Kurahashi T, Matsubara S. Org. Lett. 2011; 13: 1912
• 212c Hua R, Takeda H, Onozawa S.-y, Abe Y, Tanaka M. Org. Lett. 2007; 9: 263
• 213 Inami T, Kurahashi T, Matsubara S. Chem. Commun. 2015; 51: 1285
• 214 Liu W, Xu W, Wang J, Lu H, Xu P.-F, Wei H. Chem. Eur. J. 2021; 27: 7651
• 215 Shibata T, Sekine A, Akino M, Ito M. Chem. Commun. 2021; 57: 9048
• 216 Inami T, Takahashi T, Kurahashi T, Matsubara S. J. Am. Chem. Soc. 2019; 141: 12541
• 217 Miura T, Fujimoto Y, Funakoshi Y, Murakami M. Angew. Chem. Int. Ed. 2015; 54: 9967
• 218 Dairo TO, Woo LK. Organometallics 2017; 36: 927
• 219 Zheng R.-H, Guo H.-C, Chen T.-T, Huang Q, Huang G.-B, Jiang H.-J. RSC Adv. 2018; 8: 25123
• 220 Urriolabeitia EP, Ruiz S. Org. Biomol. Chem. 2019; 17: 2542
• 221 Kamiya I, Kawakami J.-i, Yano S, Nomoto A, Ogawa A. Organometallics 2006; 25: 3562
• 222 Pawliczek M, Garve LK. B, Werz DB. Org. Lett. 2015; 17: 1716
• 223 Bürger M, Loch MN, Jones PG, Werz DB. Chem. Sci. 2020; 11: 1912
• 224 Higashimae S, Kurata D, Kawaguchi S.-i, Kodama S, Sonoda M, Nomoto A, Ogawa A. J. Org. Chem. 2018; 83: 5267
• 225 Vahabi AH, Alizadeh A, Khavasi HR, Bazgir A. Eur. J. Org. Chem. 2017; 2017: 5347
• 226 Masuya Y, Tobisu M, Chatani N. Org. Lett. 2016; 18: 4312
• 227 Li J, Li C, Ouyang L, Li C, Yang S, Wu W, Jiang H. Adv. Synth. Catal. 2018; 360: 1138
• 228 Ishitobi K, Muto K, Yamaguchi J. ACS Catal. 2019; 9: 11685
• 229 Gómez JE, Guo W, Kleij AW. Org. Lett. 2016; 18: 6042
• 230 Shen X.-Q, Wang S.-Q, Fan D, Zhang X.-G, Tu H.-Y. J. Org. Chem. 2021; 86: 1591
• 231 Wang Y, Deng J, Chen J, Cao F, Hou Y, Yang Y, Deng X, Yang J, Wu L, Shao X, Shi T, Wang Z. ACS Catal. 2020; 10: 2707
• 232 Zhou Y, Wang Y, Lou Y, Song Q. Chem. Commun. 2019; 55: 10265
• 233 Gao Y, Gao Y, Tang X, Peng J, Hu M, Wu W, Jiang H. Org. Lett. 2016; 18: 1158