Molander, G. A.: 2020 Science of Synthesis, 2019/4: Dual Catalysis in Organic Synthesis 1 DOI: 10.1055/sos-SD-231-00168
Dual Catalysis in Organic Synthesis 1

1.2.3 Palladium/Photocatalyst Dual Catalysis

More Information

Book

Editor: Molander, G. A.

Authors: Barriault, L. ; Bhoyare, V. W.; Hashmi, A. S. K. ; He, R.; Huo, X.; Kim, U B.; Lee, S.-g.; Molander, G. A.; Muralirajan, K.; Nakao, Y.; Patil, N. T.; Primer, D. N.; Riant, O.; Rohe, S.; Rout, S. K.; Rueping, M. ; Shi, X.; Tathe, A. G.; Tellis, J. C.; Wang, J.; Zhang, W. ; Zidan, M.

Title: Dual Catalysis in Organic Synthesis 1

Print ISBN: 9783132429765; Online ISBN: 9783132429802; Book DOI: 10.1055/b-006-164899

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

 


Abstract

Palladium-catalyzed cross-coupling reactions are of great importance in chemistry. Merging palladium catalysis with photoredox catalysis has recently led to promising improvements, and typical problems associated with the use of stoichiometric oxidants, higher temperature, and harsh reaction conditions could be addressed. This chapter outlines recent developments in palladium/photoredox dual catalyzed C–C and C–N bond-formation reactions using visible-light irradiation.

 
  • 1 Alberico D, Scott ME, Lautens M. Chem. Rev.. 2007; 107: 174
  • 3 Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed.. 2009; 48: 9792
  • 4 McGlacken GP, Bateman LM. Chem. Soc. Rev.. 2009; 38: 2447
  • 7 Prier CK, Rankic DA, MacMillan DWC. Chem. Rev.. 2013; 113: 5322
  • 8 Romero NA, Nicewicz DA. Chem. Rev.. 2016; 116: 10075
  • 9 Tóth BL, Tischler O, Novák Z. Tetrahedron Lett.. 2016; 57: 4505
  • 10 Skubi KL, Blum TR, Yoon TP. Chem. Rev.. 2016; 116: 10035
  • 11 Kalyani D, McMurtrey KB, Neufeldt SR, Sanford MS. J. Am. Chem. Soc.. 2011; 133: 18566
  • 12 Zoller J, Fabry DC, Ronge MA, Rueping M. Angew. Chem. Int. Ed.. 2014; 53: 13264
  • 14 Wencel-Delord J, Dröge T, Liu F, Glorius F. Chem. Soc. Rev.. 2011; 40: 4740
  • 15 Engle KM, Mei T.-S, Wasa M, Yu J.-Q. Acc. Chem. Res.. 2012; 45: 788
  • 16 Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev.. 2002; 102: 1359
  • 17 Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed.. 2009; 48: 5094
  • 18 Basu D, Kumar S, V SS, Bandichhor R. J. Chem. Sci.. 2018; 130: 71
  • 19 Zhang M, Zhang Y, Jie X, Zhao H, Li G, Su W. Org. Chem. Front.. 2014; 1: 843
  • 20 Ford L, Jahn U. Angew. Chem. Int. Ed.. 2009; 48: 6386
  • 21 Neufeldt SR, Sanford MS. Adv. Synth. Catal.. 2012; 354: 3517
  • 22 Khan R, Boonseng S, Kemmitt PD, Felix R, Coles SJ, Tizzard GJ, Williams G, Simmonds O, Harvey J.-L, Atack J, Cox H, Spencer J. Adv. Synth. Catal.. 2017; 359: 3261
  • 23 Liang L, Xie M.-S, Wang H.-X, Niu H.-Y, Qu G.-R, Guo H.-M. J. Org. Chem.. 2017; 82: 5966
  • 24 Jiang J, Zhang W.-M, Dai J.-J, Xu J, Xu H.-J. J. Org. Chem.. 2017; 82: 3622
  • 25 Sahoo MK, Midya SP, Landge VG, Balaraman E. Green Chem.. 2017; 19: 2111
  • 26 Daugulis O, Roane J, Tran LD. Acc. Chem. Res.. 2015; 48: 1053
  • 27 Rouquet G, Chatani N. Angew. Chem. Int. Ed.. 2013; 52: 11726
  • 28 Czyz ML, Lupton DW, Polyzos A. Chem.–Eur. J.. 2017; 23: 14450
  • 29 de Meijere A, Meyer FE. Angew. Chem. Int. Ed. Engl.. 1995; 33: 2379
  • 30 Beletskaya IP, Cheprakov AV. Chem. Rev.. 2000; 100: 3009
  • 31 Dounay AB, Overman LE. Chem. Rev.. 2003; 103: 2945
  • 34 Fabry DC, Rueping M. Acc. Chem. Res.. 2016; 49: 1969
  • 35 Twilton J, Le C, Zhang P, Shaw MH, Evans RW, MacMillan DWC. Nat. Rev. Chem.. 2017; 1: 0052
  • 36 Zhang H, Huang X. Adv. Synth. Catal.. 2016; 358: 3736
  • 37 Fabry DC, Ronge MA, Rueping M. Chem.–Eur. J.. 2015; 21: 5350
  • 38 Johnston CP, Smith RT, Allmendinger S, MacMillan DWC. Nature (London). 2016; 536: 322
  • 40 Xuan J, Zhang Z.-G, Xiao W.-J. Angew. Chem. Int. Ed.. 2015; 54: 15632
  • 41 Zheng C, Cheng W.-M, Li H.-L, Na R.-S, Shang R. Org. Lett.. 2018; 20: 2559
  • 42 Wei Y, Hu P, Zhang M, Su W. Chem. Rev.. 2017; 117: 8864
  • 43 Penteado F, Lopes EF, Alves D, Perin G, Jacob RG, Lenardão EJ. Chem. Rev.. 2019; 119: 7113
  • 44 Fang P, Li M, Ge H. J. Am. Chem. Soc.. 2010; 132: 11898
  • 45 Li C, Wang L, Li P, Zhou W. Chem.–Eur. J.. 2011; 17: 10208
  • 46 Yuan Y, Chen D, Wang X. Adv. Synth. Catal.. 2011; 353: 3373
  • 48 Song H, Chen D, Pi C, Cui X, Wu Y. J. Org. Chem.. 2014; 79: 2955
  • 49 Zhou C, Li P, Zhu X, Wang L. Org. Lett.. 2015; 17: 6198
  • 50 Xu N, Li P, Xie Z, Wang L. Chem.–Eur. J.. 2016; 22: 2236
  • 51 Cheng W.-M, Shang R, Yu H.-Z, Fu Y. Chem.–Eur. J.. 2015; 21: 13191
  • 52 Zhao B, Shang R, Cheng W.-M, Fu Y. Org. Chem. Front.. 2018; 5: 1782
  • 53 Tarselli MA, Raehal KM, Brasher AK, Streicher JM, Groer CE, Cameron MD, Bohn LM, Micalizio GC. Nat. Chem.. 2011; 3: 449
  • 54 Brancale A, Silvestri R. Med. Res. Rev.. 2007; 27: 209
  • 55 Komiya M, Asano S, Koike N, Koga E, Igarashi J, Nakatani S, Isobe Y. Bioorg. Med. Chem.. 2012; 20: 6840
  • 56 Sharma UK, Gemoets HPL, Schröder F, Noël T, Van der Eycken EV. ACS Catal.. 2017; 7: 3818
  • 57 Manna MK, Bairy G, Jana R. Org. Biomol. Chem.. 2017; 15: 5899
  • 58 Trost BM, Lee C, Catalytic Asymmetric Synthesis. Ojima I. Wiley-VCH New York 2000; 593-649
  • 59 Hong AY, Stoltz BM. Eur. J. Org. Chem.. 2013; 2745
  • 60 Trost BM, Crawley ML. Top. Organomet. Chem.. 2012; 38: 321
  • 61 Kumar D, Vemula SR, Balasubramanian N, Cook GR. Acc. Chem. Res.. 2016; 49: 2169
  • 62 Sundararaju B, Achard M, Bruneau C. Chem. Soc. Rev.. 2012; 41: 4467
  • 63 Zhuo C.-X, Zheng C, You S.-L. Acc. Chem. Res.. 2014; 47: 2558
  • 64 Mishra NK, Sharma S, Park J, Han S, Kim IS. ACS Catal.. 2017; 7: 2821
  • 66 Zanoni G, Pontiroli A, Marchetti A, Vidari G. Eur. J. Org. Chem.. 2007; 3599
  • 67 Lang SB, OʼNele KM, Tunge JA. J. Am. Chem. Soc.. 2014; 136: 13606
  • 68 Xuan J, Zeng T.-T, Feng Z.-J, Deng Q.-H, Chen J.-R, Lu L.-Q, Xiao W.-J, Alper H. Angew. Chem. Int. Ed.. 2015; 54: 1625
  • 69 Zhang H.-H, Zhao J.-J, Yu S. J. Am. Chem. Soc.. 2018; 140: 16914
  • 70 Ying C.-H, Duan W.-L. Org. Chem. Front.. 2014; 1: 546
  • 71 Liao G, Li B, Chen H.-M, Yao Q.-J, Xia Y.-N, Luo J, Shi B.-F. Angew. Chem. Int. Ed.. 2018; 57: 17151
  • 72 Lee SY, Hartwig JF. J. Am. Chem. Soc.. 2016; 138: 15278
  • 73 Trost BM, Dietsch TJ. J. Am. Chem. Soc.. 1973; 95: 8200
  • 76 Dobereiner GE, Crabtree RH. Chem. Rev.. 2010; 110: 681
  • 77 Choi J, MacArthur AHR, Brookhart M, Goldman AS. Chem. Rev.. 2011; 111: 1761
  • 78 Preuster P, Papp C, Wasserscheid P. Acc. Chem. Res.. 2017; 50: 74
  • 79 Kato S, Saga Y, Kojima M, Fuse H, Matsunaga S, Fukatsu A, Kondo M, Masaoka S, Kanai M. J. Am. Chem. Soc.. 2017; 139: 2204
  • 80 Guan Z.-H, Chen M, Ren Z.-H. J. Am. Chem. Soc.. 2012; 134: 17490
  • 81 Luo S, Luo F.-X, Zhang X.-S, Shi Z.-J. Angew. Chem. Int. Ed.. 2013; 52: 10598
  • 82 Orito K, Horibata A, Nakamura T, Ushito H, Nagasaki H, Yuguchi M, Yamashita S, Tokuda M. J. Am. Chem. Soc.. 2004; 126: 14342
  • 83 Zhang H, Shi R, Gan P, Liu C, Ding A, Wang Q, Lei A. Angew. Chem. Int. Ed.. 2012; 51: 5204
  • 84 Liu K, Zou M, Lei A. J. Org. Chem.. 2016; 81: 7088
  • 85 Correa A, Martin R. J. Am. Chem. Soc.. 2009; 131: 15974
  • 86 Fujihara T, Nogi K, Xu T, Terao J, Tsuji Y. J. Am. Chem. Soc.. 2012; 134: 9106
  • 87 León T, Correa A, Martin R. J. Am. Chem. Soc.. 2013; 135: 1221
  • 89 Shimomaki K, Murata K, Martin R, Iwasawa N. J. Am. Chem. Soc.. 2017; 139: 9467
  • 90 Knölker H.-J, Reddy KR. Chem. Rev.. 2002; 102: 4303
  • 91 Tsang WCP, Zheng N, Buchwald SL. J. Am. Chem. Soc.. 2005; 127: 14560
  • 92 Jordan-Hore JA, Johansson CCC, Gulias M, Beck EM, Gaunt MJ. J. Am. Chem. Soc.. 2008; 130: 16184
  • 93 Cho SH, Yoon J, Chang S. J. Am. Chem. Soc.. 2011; 133: 5996
  • 94 Takamatsu K, Hirano K, Satoh T, Miura M. Org. Lett.. 2014; 16: 2892
  • 95 Choi S, Chatterjee T, Choi WJ, You Y, Cho EJ. ACS Catal.. 2015; 5: 4796
  • 97 Nishimura T, Onoue T, Ohe K, Uemura S. J. Org. Chem.. 1999; 64: 6750
  • 98 Nishimura T, Onoue T, Ohe K, Uemura S. Tetrahedron Lett.. 1998; 39: 6011
  • 99 Peterson KP, Larock RC. J. Org. Chem.. 1998; 63: 3185
  • 100 Kärkäs MD, Bosque I, Matsuura BS, Stephenson CRJ. Org. Lett.. 2016; 18: 5166
  • 101 Ho YA, Paffenholz E, Kim HJ, Orgis B, Rueping M, Fabry DC. ChemCatChem. 2019; 11: 1889
  • 102 Fabry DC, Zoller J, Rueping M. Org. Chem. Front.. 2019; 6: 2635