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DOI: 10.1055/a-1516-8745
Highly Efficient Synthesis of 2-Substituted Benzo[b]furan Derivatives from the Cross-Coupling Reactions of 2-Halobenzo[b]furans with Organoalane Reagents


Abstract
A highly efficient and simple route for the synthesis of 2-substituted benzo[b]furans has been developed by palladium-catalyzed cross-coupling reaction of 2-halobenzo[b]furans with aryl, alkynyl, and alkylaluminum reagents. Various 2-aryl-, 2-alkynyl-, and 2-alkyl-substituted benzo[b]furan derivatives can be obtained in 23–97% isolated yields using 2–3 mol% PdCl2/4–6 mol% XantPhos as the catalyst under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in 2-halobenzo[b]furans gave products in 40–97% isolated yields. In addition, aluminum reagents containing thienyl, furanyl, trimethylsilanyl, and benzyl groups worked efficiently with 2-halobenzo[b]furans as well, and three bioactive molecules with 2-substituted benzo[b]furan skeleton were synthesized. Furthermore, the broad substrates scope and the typical maintenance of vigorous efficiency on gram scale make this protocol a potentially practical method to synthesize 2-substituted benzo[b]furan derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.
Key words
2-substituted benzo[b]furans - palladium - organoalane reagents - 2-halobenzo[b]furan - cross-coupling reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1516-8745.
- Supporting Information
Publikationsverlauf
Eingereicht: 07. Mai 2021
Angenommen nach Revision: 25. Mai 2021
Accepted Manuscript online:
25. Mai 2021
Artikel online veröffentlicht:
24. Juni 2021
© 2021. Thieme. All rights reserved
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References
- 1a Hou X.-L, Yang Z, Wong HN. C. Progress in Heterocyclic Chemistry . Gribble GW, Gilchrist TL. Pergamon; Oxford: 2003
- 1b Donnelly DM. X, Meegan MJ. I. In Comprehensive Heterocyclic Chemistry, Vol. 4. Katritzky AR, Rees CW. Pergamon; New York: 1984
- 1c Sill MC, Das AK, Itou T, Karmakar S, Mukherjee PK, Mizuguchi H, Kashiwada Y, Fukui H, Nemoto H. Bioorg. Med. Chem. 2015; 23: 6869
- 1d Simonetti SO, Larghi EL, Bracca AB. J, Kaufman TS. Nat. Prod. Rep. 2013; 30: 941
- 2a Castro CE, Gaughan EJ, Owsley DC. J. Org. Chem. 1966; 31: 4071
- 2b Somei M, Yamada F. Nat. Prod. Rep. 2004; 21: 278
- 2c Zhang J, Li L, Wang Y, Wang W, Xue J, Li Y. Org. Lett. 2012; 14: 4528
- 3 Hwang J.-W, Choi D.-H, Jeon J.-H, Kim J.-K, Jun J.-G. Bull. Korean Chem. Soc. 2010; 31: 965
- 4a Erber S, Ringshandl R, von Angerer E. Anti-Cancer Drug Des. 1991; 6: 417
- 4b Galal SA, Abd El-Al AS, Abdallah MM, El-Diwani HI. Bioorg. Med. Chem. Lett. 2009; 19: 2420
- 4c Kucuksayan E, Ozben T. Curr. Top. Med. Chem. 2017; 17: 907
- 5a Kim S, Salim AA, Swanson SM, Kinghorn AD. Anticancer Agents Med. Chem. 2006; 6: 319
- 5b Zaher AF, Abuel-Maaty SM, El-Nassan HB, Amer SA. S, Abdelghany TM. J. Enzyme Inhib. Med. Chem. 2016; 31: 145
- 5c Ghorab MM, Ragab FA, Heiba HI, Soliman AM. Eur. J. Med. Chem. 2016; 117: 8
- 6a Lau CK, Bélanger PC, Scheigetz J, Dufresne C, Williams HW. R, Maycock AL, Guindon Y, Bach T, Dallob AL, Denis D, Ford-Hutchinson AW, Gale PH, Hopple SL, Letts LG, Luell S, McFarlane CS, MacIntyre E, Meurer R, Miller DK, Piechuta H, Riendeau D, Rokach J, Rouzer C. J. Med. Chem. 1989; 32: 1190
- 6b Ohemeng KA, Apollina MA, Nguyen VN, Schwender CF, Singer M, Steber M, Ansell J, Argentieri D, Hageman W. J. Med. Chem. 1994; 37: 3663
- 7a Aslam SN, Stevenson PC, Phythian SJ, Veitch NC, Hall DR. Tetrahedron 2006; 62: 4214
- 7b Hiremathad A, Patil MR, Chethana KR, Chand K, Santos MA, Keri RS. RSC Adv. 2015; 5: 96809
- 7c He W, Xu B, Bao J, Deng X, Liu W, Zhang Y, Jiang F, Fu L. Med. Chem. Res. 2016; 25: 2485
- 8 Bowyer PW, Tate EW, Leatherbarrow RJ, Holder AA, Smith DF, Brown KA. ChemMedChem 2008; 3: 402
- 9a Tang H.-J, Zhang X.-W, Yang L, Li W, Li J.-H, Wang J.-X, Chen J. Eur. J. Med. Chem. 2016; 124: 637
- 9b Khan MW, Alam MJ, Rashid MA, Chowdhury R. Bioorg. Med. Chem. 2005; 13: 4796
- 10 Halabalaki M, Alexi X, Aligiannis N, Alexis MN, Skaltsounis A.-L. J. Nat. Prod. 2008; 71: 1934
- 11a Manarin F, Roehrs JA, Gay RM, Brandão R, Menezes PH, Nogueira CW, Zeni G. J. Org. Chem. 2009; 74: 2153
- 11b Huang X.-C, Wang F, Liang Y, Li J.-H. Org. Lett. 2009; 11: 1139
- 11c Yin S.-C, Zhou Q, Zhao X.-Y, Shao L.-X. J. Org. Chem. 2015; 80: 8916
- 11d Zhao X, Zhang L.-P, Lu X.-Y, Li T.-J, Lu K. J. Org. Chem. 2015; 80: 2918
- 12a Ota T, Hasegawa S, Inoue S, Sato K. J. Chem. Soc., Perkin Trans. 1 1988; 3029
- 12b Watanabe M, Date M, Kawanishi K, Hori T, Furukawa S. Chem. Pharm. Bull. 1991; 39: 41
- 12c Fuerst DE, Stoltz BM, Wood JL. Org. Lett. 2000; 2: 3521
- 12d Miyata O, Takeda N, Morikami Y, Naito T. Org. Biomol. Chem. 2003; 1: 254
- 12e Pan C, Yu J, Zhou Y, Wang Z, Zhou M.-M. Synlett 2006; 1657
- 12f Rao ML. N, Awasthi DK, Banerjee D. Tetrahedron Lett. 2007; 48: 431
- 13a Bach T, Bartels M. Synlett 2001; 1284
- 13b Zhang H, Ferreira EM, Stoltz BM. Angew. Chem. Int. Ed. 2004; 43: 6144
- 13c Xie X, Chen B, Lu J, Han J, She X, Pan X. Tetrahedron Lett. 2004; 45: 6235
- 13d Willis MC, Taylor D, Gillmore AT. Org. Lett. 2004; 6: 4755
- 13e DiMauro E, Vitullo JR. J. Org. Chem. 2006; 71: 3959
- 13f Liang Y, Tang S, Zhang X.-D, Mao L.-Q, Xie Y.-X, Li J.-H. Org. Lett. 2006; 8: 3017
- 13g Nagamochi M, Fang Y.-Q, Lautens M. Org. Lett. 2007; 9: 2955
- 13h Csékei M, Novák Z, Kotschy A. Tetrahedron 2008; 64: 8992
- 13i Hussain M, Hung NT, Langer P. Tetrahedron Lett. 2009; 50: 3929
- 14a Fürstner A, Davies PW. J. Am. Chem. Soc. 2005; 127: 15024
- 14b Witham CA, Huang W.-Y, Tsung CK, Kuhn JN, Somorjai GA, Toste FD. Nat. Chem. 2010; 2: 36
- 14c Li Y.-M, Liu J.-H, Witham CA, Huang W.-Y, Marcus MA, Fakra SC, Alayoglu P, Zhu Z.-W, Thompson CM, Arjun A, Lee K, Gross E, Toste FD, Somorjai GA. J. Am. Chem. Soc. 2011; 133: 13527
- 15a Ref. 13f.
- 15b Huang W.-Y, Liu J.-H, Alayoglu P, Li Y.-M, Witham CA, Tsung C.-K, Toste FD, Somorjai GA. J. Am. Chem. Soc. 2010; 132: 16771
- 15c Kim M, Lee S, Kim K, Shin D, Kim H, Song H. Chem. Commun. 2014; 50: 14938
- 15d Rubio-Marques P, Rivero-Crespo MA, Leyva-Perez A, Corma A. J. Am. Chem. Soc. 2015; 137: 11832
- 15e Chen J, Liu M, Wang X, Wang X, Ding J, Wu H. Synthesis 2013; 45: 2241
- 16 Zhang Y, Xin Z.-J, Xue J.-J, Li Y. Chin. J. Chem. 2008; 26: 1461
- 17a Belting V, Krause N. Org. Lett. 2006; 8: 4489
- 17b Hashmi AS. K, Ramamurthi TD, Rominger F. Adv. Synth. Catal. 2010; 352: 971
- 17c Morozov OS, Lunchev AV, Bush AA, Tukov AA, Asachenko AF, Khrustalev VN, Zalesskiy SS, Ananikov VP, Nechaev MS. Chem. Eur. J. 2014; 20: 6162
- 17d Kong L.-B, Ganguly R, Li Y.-X, Kinjo R. Chem. Sci. 2015; 6: 2893
- 17e Xia Z.-H, Khaled O, Mouriès-Mansuy V, Ollivier C, Fensterbank L. J. Org. Chem. 2016; 81: 7182
- 17f Zhao J, Nguyen SC, Ye R, Ye B.-H, Weller H, Somorjai GA, Alivisatos AP. F, Toste D. ACS Cent. Sci. 2017; 3: 482
- 18a Trost BM, McClory A. Angew. Chem. Int. Ed. 2007; 46: 2074
- 18b Isono N, Lautens M. Org. Lett. 2009; 11: 1329
- 18c Boyer A, Isono N, Lackner S, Lautens M. Tetrahedron 2010; 66: 6468
- 18d Sarbajna A, Pandey P, Rahaman SM. W, Singh K, Tyagi A, Dixneuf PH, Bera JK. ChemCatChem 2017; 9: 1397
- 19 Li X.-W, Chianese AR, Vogel T, Carbtree RT. Org. Lett. 2005; 7: 5437
- 20 Nakamura M, Ilies L, Otsubo S, Nakamura E. Angew. Chem. Int. Ed. 2006; 45: 944
- 21a Hiroya K, Itoh S, Sakamoto T. Tetrahedron 2005; 61: 10958
- 21b Nakamura M, Ilies L, Otsubo S, Nakamura E. Org. Lett. 2006; 8: 2803
- 21c Liu J, Zhang N, Yue Y, Wang D, Zhang Y, Zhang X, Zhuo K. RSC Adv. 2013; 3: 3865
- 21d Pu W.-C, Mu G.-M, Zhang G.-L, Wang C. RSC Adv. 2014; 4: 903
- 22a Gil-Moltó J, Nájera C. Eur. J. Org. Chem. 2005; 19: 4073
- 22b Ohtaka A, Teratani T, Fujii R, Ikeshita K, Kawashima T, Tatsumi K, Shimomura O, Nomura R. J. Org. Chem. 2011; 76: 4052
- 22c Priyadarshini S, Amal-J PJ, Srinivas P, Maheswaran H, Lakshmi Kantam M, Bhargava S. Tetrahedron Lett. 2011; 52: 1615
- 22d Cano R, Yus M, Ramon DJ. Tetrahedron 2012; 68: 1393
- 22e Zhou R, Wang W, Jiang Z.-J, Wang K, Zheng X.-L, Fu H.-Y, Chen H, Li R.-X. Chem. Commun. 2014; 50: 6023
- 22f Yum EK, Yang O.-K, Kim J.-E, Park HJ. Bull. Korean Chem. Soc. 2013; 34: 2645
- 22g Chahdoura F, Mallet-Ladeira S, Gomez M. Org. Chem. Front. 2015; 2: 312
- 22h Mandali PK, Chand DK. Synthesis 2015; 47: 1661
- 22i Bruneau A, Gustafson KP. J, Yuan N, Tai C.-W, Persson I, Zou X, Bäckvall JE. B. Chem. Eur. J. 2017; 23: 12886
- 22j Bhadra M, Sasmal HS, Basu A, Midya SP, Kandambeth S, Pachfule P, Balaraman E, Banerjee R. ACS Appl. Mater. Interfaces 2017; 9: 13785
- 22k Ji G.-J, Duan Y.-N, Zhang S.-C, Yang Y. Catal. Today 2019; 330: 101
- 23a Doad GJ. S, Barltrop JA, Pretty CM, Owen TC. Tetrahedron Lett. 1989; 30: 1597
- 23b Okuro K, Furuune M, Enna M, Miura M, Nomura M. J. Org. Chem. 1993; 58: 4716
- 23c Bates CG, Saejueng P, Murphy JM, Venkataraman D. Org. Lett. 2002; 4: 4727
- 23d Li J.-H, Li J.-L, Wang D.-P, Pi S.-F, Xie Y.-X, Zhang M.-B, Hu X.-C. J. Org. Chem. 2007; 72: 2053
- 23e Jaseer EA, Prasad DJ. C, Sekar G. Tetrahedron 2010; 66: 2077
- 23f Zeng W, Wu W.-Q, Jiang H.-F, Huang L.-B, Sun Y.-D, Chen Z.-W, Li X.-W. Chem. Commun. 2013; 49: 6611
- 23g Ref. 22g.
- 23h Moure MJ, SanMartin R, Domínguez E. Adv. Synth. Catal. 2014; 356: 2070
- 24a Carril M, Correa A, Bolm C. Angew. Chem. Int. Ed. 2008; 47: 4862
- 24b Yang J.-G, Shen G.-D, Chen D.-B. Synth. Commun. 2013; 43: 837
- 25a Wang Z, Elokdah H, McFarlane G, Pan S, Antane M. Tetrahedron Lett. 2006; 47: 3365
- 25b Kitamura Y, Sako S, Udzu T, Tsutsui A, Maegawa T, Monguchi Y, Sajiki H. Chem. Commun. 2007; 5069
- 25c Molander GA, Canturk B, Kennedy LE. J. Org. Chem. 2009; 74: 973
- 25d Denmark SE, Smith RC, Chang WT, Muhuhi JM. J. Am. Chem. Soc. 2009; 131: 3104
- 25e Fang H, Guo L, Zhang Y, Yao W, Huang Z. Org. Lett. 2016; 18: 5624
- 26a Lin S.-Y, Chen C.-L, Lee Y.-J. J. Org. Chem. 2003; 68: 2968
- 26b Thielges S, Meddah E, Bisseret P, Eustache J. Tetrahedron Lett. 2004; 45: 907
- 26c Gill GS, Grobelny DW, Chaplin JH, Flynn BL. J. Org. Chem. 2008; 73: 1131
- 26d James CA, Coelho AL, Gevaert M, Forgione P, Snieckus V. J. Org. Chem. 2009; 74: 4094
- 26e Alvey L, Prado S, Saint-Joanis B, Michel S, Koch M, Cole ST, Tillequin F, Janin YL. Eur. J. Med. Chem. 2009; 44: 2497
- 26f Rao ML. N, Jadhav DN, Venkatesh V. Eur. J. Org. Chem. 2009; 4300
- 26g Hung N.-T, Hussain M, Malik I, Villinger A, Langer P. Tetrahedron Lett. 2010; 51: 2420
- 26h Rao ML. N, Jadhav DN, Dasgupta P. Org. Lett. 2010; 12: 2048
- 26i Rao ML. N, Banerjee D, Dhanorkar RJ. Tetrahedron 2010; 66: 3623
- 26j Rao ML. N, Venkatesh V, Jadhav DN. Eur. J. Org. Chem. 2010; 3945
- 26k Quasdorf KW, Antoft-Finch A, Liu P, Silberstein AL, Komaromi A, Blackburn T, Ramgren SD, Houk KN, Snieckus V, Garg NK. J. Am. Chem. Soc. 2011; 133: 6352
- 26l Rao ML. N, Awasthi DK, Talode JB. Tetrahedron Lett. 2012; 53: 2662
- 27a Hu J, Liu L, Wang X.-C, Hu Y.-Y, Yang S.-D, Liang Y.-M. Green Sustainable Chem. 2011; 1: 165
- 27b Damera K, Ke B, Wang K, Dai C, Wang L, Wang B. RSC Adv. 2012; 2: 9403
- 27c Siddiqui IR, Waseem MA, Shamim S, Shireen AS, Srivastava A. Tetrahedron Lett. 2013; 54: 4154
- 27d Sun S.-X, Wang J.-J, Xu Z.-J, Cao L.-Y, Shi Z.-F, Zhang H.-L. Tetrahedron 2014; 70: 3798
- 27e Liu Y, Lu T, Tang W.-F, Gao J. RSC Adv. 2018; 8: 28637
- 28 Protti S, Fagnoni M, Albini A. J. Org. Chem. 2012; 77: 6473
- 29a Singh FV, Wirth T. Synthesis 2012; 44: 1171
- 29b Liu L, Ji X.-Y, Dong J.-Y, Zhou Y.-B, Yin S.-F. Org. Lett. 2016; 18: 3138
- 29c Singh FV, Mangaonkar SR. Synthesis 2018; 50: 4940
- 30 Takeda N, Miyata O, Naito T. Eur. J. Org. Chem. 2007; 9: 1491
- 31a Yuan Y, Men H.-B, Lee C. J. Am. Chem. Soc. 2004; 126: 14720
- 31b Ghosh S, Das J. Tetrahedron Lett. 2011; 52: 1112
- 32a Wu K.-H, Gau H.-M. J. Am. Chem. Soc. 2006; 128: 14808
- 32b Wu K.-H, Chen C.-A, Gau H.-M. Angew. Chem. Int. Ed. 2007; 46: 5373
- 32c Wu K.-H, Chuang D.-W, Chen C.-A, Gau H.-M. Chem.Commun. 2008; 20: 2343
- 32d Zhou S.-L, Wu K.-H, Chen C.-A, Gau H.-M. J. Org. Chem. 2009; 74: 3500
- 32e Hawner C, Müller D, Gremaud L, Felouat A, Woodward S, Alexakis A. Angew. Chem. Int. Ed. 2010; 49: 7769
- 32f Zhou Y, Lecourt T, Micouin L. Angew. Chem. Int. Ed. 2010; 49: 2607
- 32g Gremaud L, Alexakis A. Angew. Chem. Int. Ed. 2012; 51: 794
- 32h Andrews P, Latham CM, Magre M, Willcox D, Woodward S. Chem. Commun. 2013; 49: 1488
- 32i Kolb A, von Zezschwitz P. Top. Organomet. Chem. 2013; 41: 245
- 33a Baba S, Negishi E. J. Am. Chem. Soc. 1976; 98: 6729
- 33b Takai K, Oshima K, Nozaki H. Tetrahedron Lett. 1980; 21: 2531
- 33c Blum J, Gelman D, Baidossi W, Shakh E, Rosenfeld A, Aizenshtat Z, Wassermann BC, Frick M, Heymer B, Schutte S, Wernik S, Schumann H. J. Org. Chem. 1997; 62: 8681
- 33d Link JT. Org. React. 2002; 60: 157
- 33e Qian M.-X, Huang Z, Negishi E. Org. Lett. 2004; 6: 1531
- 33f Cooper T, Novak A, Humphreys LD, Walker MD, Woodward S. Adv. Synth. Catal. 2006; 348: 686
- 33g Zhou S.-L, Yang Z.-Y, Chen X, Li Y.-M, Zhang L.-J, Fang H, Wang W, Zhu X.-C, Wang SW. J. Org. Chem. 2015; 80: 6323
- 33h Li Q.-H, Shao X.-B, Ding Y, Wen C, Zhao Z.-G. Curr. Org. Chem. 2018; 22: 1523
- 33i Shang R, Ilies L, Nakamura E. J. Am. Chem. Soc. 2015; 137: 7660
- 33j Shang R, Ilies L, Nakamura E. J. Am. Chem. Soc. 2016; 138: 10132
- 33k Wang H.-Q, Zhang S.-Z, Wang Z.-Q, He M.-H, Xu K. Org. Lett. 2016; 18: 5628
- 33l Li QH, Wang J.-H, Wen C, Xin J, Cao K.-P, Wu K, Liang M. Chin. Chem. Lett. 2019; 30 in press; DOI: 10.1016/j.cclet.2019.02.028
- 34a Ku S.-L, Hui X.-P, Chen C.-A, Kuo Y.-Y, Gau H.-M. Chem. Commun. 2007; 43: 3847
- 34b Biradar DB, Gau H.-M. Chem. Commun. 2011; 47: 10467
- 34c Groll K, Blümke TD, Unsinn A, Haas D, Knochel P. Angew. Chem. Int. Ed. 2012; 51: 11157
- 34d Ogawa H, Yang Z.-K, Minami H, Kojima K, Saito T, Wang C, Uchiyama M. ACS Catal. 2017; 7: 3988
- 35a Biradar DB, Gau H.-M. Org. Biomol. Chem. 2012; 10: 4243
- 35b Chen X, Zhou L.-M, Li Y.-M, Xie T, Zhou S.-L. J. Org. Chem. 2014; 79: 230
- 36a Li Q.-H, Gau H.-M. Synlett 2012; 5: 747
- 36b Li Q.-H, Jeng J.-Y, Gau H.-M. Eur. J. Org. Chem. 2014; 35: 7916
- 36c Li Q.-H, Liao J.-W, Huang Y.-L, Chiang R.-T, Gau H.-M. Org. Biomol. Chem. 2014; 38: 7634
- 36d Zhang Z, Mo S, Zhang G, Shao X.-B, Li Q.-H, Zhong Y. Synlett 2017; 28: 611
- 36e Zhang Z, Shao X.-B, Zhang G, Li Q.-H, Li X.-Y. Synthesis 2017; 49: 3643
- 36f Li Q.-H, Ding Y, Zhang G, Zhang Z, Mo S. Curr. Org. Synth. 2017; 14: 462
- 36g Shao X.-B, Zhang Z, Li Q.-H, Zhao Z.-G. Org. Biomol. Chem. 2018; 16: 4797
- 36h Shao X.-B, Wen C, Zhang G, Cao K.-P, Wu L, Li Q.-H. J. Organomet. Chem. 2018; 870: 68
- 36i Shao X.-B, Jiang X, Li Q.-H, Zhao Z.-G. Tetrahedron 2018; 74: 6063
- 36j Mo S, Shao X.-B, Zhang G, Li Q.-H. RSC Adv. 2017; 7: 27243
- 36k Zhang G, Wu K, Wen C, Li Q.-H. J. Organomet. Chem. 2020; 906, 121040
- 37 Ye C, Li Y, Bao H. Adv. Synth. Catal. 2017; 359: 3720
- 38 Vasin VA, Fadin MV, Tarasova IV. Russ. J. Org. Chem. 2018; 53: 1815
For selected Pt-catalyzed examples, see:
For selected Pd-catalyzed examples, see:
For selected Au-catalyzed examples, see:
For selected Rh-catalyzed examples, see:
For Cu-catalyzed examples, see:
For selected recent reports on Pd-catalyzed examples, see:
For selected recent reports on Cu-catalyzed examples, see:
For selected recent reports on the addition to carbonyl compounds, see:
For selected recent reports on the cross-coupling reactions, see: