Recent Applications on Dual-Catalysis for C–C and C–X Cross-Coupling Reactions

Dedicated to Prof. Günter Helmchen on the occasion of his 81^st birthday

Abstract

Coupling reactions stand amid the most significant reactions in synthetic organic chemistry. Of late, these coupling strategies are being viewed as a versatile synthetic tool for a wide range of organic transformations in many sectors of chemistry, ranging from indispensable synthetic scaffolds and natural products of biological significance to novel organic materials. Further, the use of dual-catalysis in accomplishing various interesting cross-coupling transformations is an emerging field in synthetic organic chemistry, owing to their high catalytic performance rather than the use of a single catalyst. In recent years, synthetic organic chemists have given considerable attention to hetero-dual catalysis; wherein these catalytic systems have been employed for the construction of versatile carbon–carbon [C(sp ³)–C(sp ³), C(sp ³)–C(sp ²), C(sp ²)–C(sp ²)] and carbon–heteroatom (C–N, C–O, C–P, C–S) bonds. Therefore, in this mini-review, we are emphasizing recently developed various cross-coupling reactions catalysed by transition-metal dual-catalysis (i.e., using palladium and copper catalysts, but omitting the reports on photoredox/metal catalysis).

1 Introduction

2 Cu/Pd-Catalysed Bond Formation

2.1 Pd/Cu-Catalysed C(sp ³)–C(sp ²) Bond Formation

2.2 Pd/Cu-Catalysed C(sp ²)–C(sp ²) Bond Formation

2.3 Pd/Cu-Catalysed C(sp)–C(sp ²) Bond Formation

2.4 Pd/Cu-Catalysed C(sp ³)–C(sp ³) Bond Formation

2.5 Pd/Cu-Catalysed C–X (X = B, N, P, S, Si) Bond Formation

3 Conclusion

Key words

dual-metal catalysis - cross-coupling reactions - Kinugasa reaction - palladium catalysis - heterocycles

Publication History

Received: 16 June 2022

Accepted after revision: 11 July 2022

Accepted Manuscript online:
11 July 2022

Article published online:
03 August 2022

• References

• 1 Carsten B. J. Org. Chem. 2012; 77: 5221
• 2 Pérez Sestelo J, Sarandeses LA. Molecules 2020; 25: 4500
• 3 Ayogu JI, Onoabedje EA. Catal. Sci. Technol. 2019; 9: 5233
• 4 Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
• 5 Dombrowski AW, Gesmundo NJ, Aguirre AL, Sarris KA, Young JM, Bogdan AR, Martin MC, Gedeon S, Wang Y. Med. Chem. Lett. 2020; 11: 597
• 6 Rayadurgam J, Sana S, Sasikumar M, Gu Q. Org. Chem. Front. 2021; 8: 384
• 7 Magano J, Dunetz JR. Chem. Rev. 2011; 111: 2177
• 8 Hooshmand SE, Heidari B, Sedghi R, Varma RS. Green Chem. 2019; 21: 381
• 9 Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 20: 3437
• 10 Farina V, Krishnamurthy V, Scott WJ. Organic Reactions, Vol. 50. John Wiley & Sons; 1997
• 11 Cordovilla C, Bartolomé C, Martínez-Ilarduya JM, Espinet P. ACS Catal. 2015; 5: 3040
• 12 Stille JK. Angew. Chem., Int. Ed. Engl. 1986; 25: 508
• 13 Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
• 14 Li H, Johansson Seechurn CC. C, Colacot TJ. ACS Catal. 2012; 2: 1147
• 15 Fleckenstein CA, Plenio H. Chem. Soc. Rev. 2010; 39: 694
• 16 Guerrero Rios I, Rosas-Hernandez A, Martin E. Molecules 2011; 16: 970
• 17 Surry DS, Buchwald SL. Chem. Sci. 2010; 2: 27
• 18 Hartwig JF. Acc. Chem. Res. 2008; 41: 1534
• 19 Fan M, Zhou W, Jiang Y, Ma D. Angew. Chem. Int. Ed. 2016; 55: 6211
• 20 Lagishetti C, Banne S, You H, Tang M, Guo J, Qi N, He Y. Org. Lett. 2019; 21: 5301
• 21 You H, Vegi SR, Lagishetti C, Chen S, Reddy RS, Yang X, Guo J, Wang C, He Y. J. Org. Chem. 2018; 83: 4119
• 22 Zhou C, Ma D. Chem. Commun. 2014; 50: 3085
• 23 Aneeja T, Neetha M, Afsina CM. A, Anilkumar G. RSC Adv. 2020; 10: 34429
• 24 Zhou Y, Zhang Z, Jiang Y, Pan X, Ma D. Synlett 2015; 26: 1586
• 25 Klapars A, Antilla JC, Huang X, Buchwald SL. J. Am. Chem. Soc. 2001; 123: 7727
• 26 Hayashi Y. Chem. Sci. 2016; 7: 866
• 27 Ramesh K, Satyanarayana G. J. Org. Chem. 2017; 82: 4254
• 28 Ghora S, Sreenivasulu C, Satyanarayana G. Synthesis 2022; 54: 393
• 29 Reddy AG. K, Krishna J, Satyanarayana G. ChemistrySelect 2016; 1: 1151
• 30 Kumar DR, Panigrahy RS, Ravi Kishore D, Satyanarayana G. ChemistrySelect 2019; 4: 12111
• 31 Beccalli EM, Broggini G, Gazzola S, Mazza A. Org. Biomol. Chem. 2014; 12: 6767
• 32 Mateos J, Rivera-Chao E, Fañanás-Mastral M. ACS Catal. 2017; 7: 5340
• 33 Friis SD, Pirnot MT, Dupuis LN, Buchwald SL. Angew. Chem. Int. Ed. 2017; 56: 7242
• 34 Allen AE, MacMillan DW. C. Chem. Sci. 2012; 3: 633
• 35 Sammis GM, Danjo H, Jacobsen EN. J. Am. Chem. Soc. 2004; 126: 9928
• 36 Romiti F, del Pozo J, Paioti PH. S, Gonsales SA, Li X, Hartrampf FW. W, Hoveyda AH. J. Am. Chem. Soc. 2019; 141: 17952
• 37 Kim UB, Jung DJ, Jeon HJ, Rathwell K, Lee S. Chem. Rev. 2020; 120: 13382
• 38 Singh S, Roy VJ, Dagar N, Sen PP, Roy SR. Adv. Synth. Catal. 2021; 363: 937
• 39 Lichosyt D, Zhang Y, Hurej K, Dydio P. Nat. Catal. 2019; 2: 114
• 40 Wang D, Malmberg R, Pernik I, Prasad SK. K, Roemer M, Venkatesan K, Schmidt TW, Keaveney ST, Messerle BA. Chem. Sci. 2020; 11: 6256
• 41 Gui Y.-Y, Sun L, Lu Z.-P, Yu D.-G. Org. Chem. Front. 2016; 3: 522
• 42 Skubi KL, Blum TR, Yoon TP. Chem. Rev. 2016; 116: 10035
• 43 Wasilke J.-C, Obrey SJ, Baker RT, Bazan GC. Chem. Rev. 2005; 105: 1001
• 44 Mukherjee S, Biswas B. ChemistrySelect 2020; 5: 10704
• 45 Dub PA, Gordon JC. ACS Catal. 2017; 7: 6635
• 46 Shibasaki M, Kanai M, Matsunaga S, Kumagai N. Acc. Chem. Res. 2009; 42: 1117
• 47 Uraguchi D, Kinoshita N, Kizu T, Ooi T. J. Am. Chem. Soc. 2015; 137: 13768
• 48 Sun W, He C, Liu T, Duan C. Chem. Commun. 2019; 55: 3805
• 49 Chan Y.-C, Bai Y, Chen W.-C, Chen H.-Y, Li C.-Y, Wu Y.-Y, Tseng M.-C, Yap GP. A, Zhao L, Chen H.-Y, Ong T.-G. Angew. Chem. Int. Ed. 2021; 60: 19949
• 50 Chen G, Wang Y, Zhao J, Zhang X, Fan X. J. Org. Chem. 2021; 86: 14652
• 51 Luo H, Li Y, Du L, Xin X, Wang T, Han J, Tian Y, Li B. Org. Lett. 2021; 23: 7883
• 52 Li Y, Luo H, Tang Z, Li Y, Du L, Xin X, Li S, Li B. Org. Lett. 2021; 23: 6450
• 53 Wang C, Xi Z. Chem. Soc. Rev. 2007; 36: 1395
• 54 Clerc A, Marelli E, Adet N, Monot J, Martín-Vaca B, Bourissou D. Chem. Sci. 2021; 12: 435
• 55 Zhong C, Shi X. Eur. J. Org. Chem. 2010; 2010: 2999
• 56 Zhou Q.-L. Angew. Chem. Int. Ed. 2016; 55: 5352
• 57 Du Z, Shao Z. Chem. Soc. Rev. 2013; 42: 1337
• 58 Chen D.-F, Gong L.-Z. J. Am. Chem. Soc. 2022; 144: 2415
• 59 Rueping M, Koenigs RM, Atodiresei I. Chem. Eur. J. 2010; 16: 9350
• 60 Li C, Villa-Marcos B, Xiao J. J. Am. Chem. Soc. 2009; 131: 6967
• 61 Volla CM. R, Fava E, Atodiresei I, Rueping M. Chem. Commun. 2015; 51: 15788
• 62 Afewerki S, Córdova A. Chem. Rev. 2016; 116: 13512
• 63 Xu M.-M, Wang H.-Q, Mao Y.-J, Mei G.-J, Wang S.-L, Shi F. J. Org. Chem. 2018; 83: 5027
• 64 Liu H, Han Y.-F, Gao Z.-H, Zhang C.-L, Wang C, Ye S. ACS Catal. 2022; 12: 1657
• 65 Zhang J, Gao Y.-S, Gu B.-M, Yang W.-L, Tian B.-X, Deng W.-P. ACS Catal. 2021; 11: 3810
• 66 Ling B, Yang W, Wang Y.-E, Mao J. Org. Lett. 2020; 22: 9603
• 67 Wang MH, Scheidt KA. Angew. Chem. Int. Ed. 2016; 55: 14912
• 68 Cardinal-David B, Raup DE. A, Scheidt KA. J. Am. Chem. Soc. 2010; 132: 5345
• 69 Cohen DT, Scheidt KA. Chem. Sci. 2011; 3: 53
• 70 Singha S, Patra T, Daniliuc CG, Glorius F. J. Am. Chem. Soc. 2018; 140: 3551
• 71 Suliman AM. Y, Ahmed E.-AM. A, Gong T.-J, Fu Y. Org. Lett. 2021; 23: 3259
• 72 Schuppe AW, Knippel JL, Borrajo-Calleja GM, Buchwald SL. J. Am. Chem. Soc. 2021; 143: 5330
• 73 Mateos J, Fuentes-Vara N, Fra L, Rivera-Chao E, Vázquez-Galiñanes N, Chaves-Pouso A, Fañanás-Mastral M. Organometallics 2020; 39: 740
• 74 Piou T, Slutskyy Y, Kevin NJ, Sun Z, Xiao D, Kong J. Org. Lett. 2021; 23: 1996
• 75 Al Mamari HH, Grošelj U, Požgan F, Brodnik H. J. Org. Chem. 2021; 86: 3138
• 76 Li W, Tang J, Li S, Zheng X, Yuan M, Xu B, Jiang W, Fu H, Li R, Chen H. Org. Lett. 2020; 22: 7814
• 77 Komiyama T, Minami Y, Furuya Y, Hiyama T. Angew. Chem. Int. Ed. 2018; 57: 1987
• 78 Jeanne-Julien L, Masson G, Kouoi R, Regazzetti A, Genta-Jouve G, Gandon V, Roulland E. Org. Lett. 2019; 21: 3136
• 79 Xue S, Lücht A, Benet-Buchholz J, Kleij AW. Chem. Eur. J. 2021; 27: 10107
• 80 Zhang C, Wu X, Wang C, Zhang C, Qu J, Chen Y. Org. Lett. 2020; 22: 6376
• 81 Wei W, Li X, Gu M, Yao H, Lin A. Org. Biomol. Chem. 2017; 15: 8458
• 82 Khakyzadeh V, Rostami A, Veisi H, Shaghasemi BS, Reimhult E, Luque R, Xia Y, Darvishi S. Org. Biomol. Chem. 2019; 17: 4491
• 83 Takeda Y, Shibuta K, Aoki S, Tohnai N, Minakata S. Chem. Sci. 2019; 10: 8642
• 84 Yuan Y, Wu F.-P, Xu J.-X, Wu X.-F. Angew. Chem. Int. Ed. 2020; 59: 17055
• 85 Khangarot RK, Kaliappan KP. Eur. J. Org. Chem. 2013; 2013: 7664
• 86 Santoro S, Himo F. J. Org. Chem. 2021; 86: 10665
• 87 Malig TC, Yu D, Hein JE. J. Am. Chem. Soc. 2018; 140: 9167
• 88 Qi J, Wei F, Tung C.-H, Xu Z. Angew. Chem. Int. Ed. 2021; 60: 13814
• 89 Dorn SK, Brown MK. ACS Catal. 2022; 12: 2058