2.7 Cobalt-Catalyzed Cross-Coupling Reactions

P. Schiltz; M. Gao; C. Gosmini 

Abstract

Transition-metal-catalyzed cross-coupling reactions have been an essential strategy for the construction of C—C bonds, including in the syntheses of pharmaceuticals and natural products, since the pioneering work of Heck, Negishi, and Suzuki, among others. Of the widely applied catalysts based on group 8–10 metals, economical cobalt salts have been shown to be advantageous as an alternative to other commonly used expensive and/or toxic catalysts. In this review, cobalt-catalyzed cross-coupling reactions of organometallic reagents, such as organomagnesium or organozinc derivatives, to achieve the formation of C—C bonds, are summarized. Furthermore, various methods for the cobalt-catalyzed reductive cross coupling of C—X/C—O electrophiles have also been reported for selective C—C bond formation, and these are also discussed.

Schlüsselwörter

base-metal catalysis - cobalt catalysis - cross-coupling reactions - Grignard reagents - organozinc compounds - carbon–carbon bond formation - electrophiles - reductive coupling - Negishi coupling - Kumada coupling

• 1 Marsden JA, Haley MM, In: Metal-Catalyzed Cross-Coupling Reactions de Meijere A, Diederich F. Wiley-VCH Weinheim, Germany 2004; 317

• 2 Knochel P. Handbook of Functionalized Organometallics: Applications in Synthesis. Wiley-VCH; Weinheim, Germany 2005

• 3 Johansson Seechurn CCC, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062

• 4 Corbet J.-P, Mignani GC. Chem. Rev. 2006; 106: 2651

• 5 Choi J, Fu GC. Science (Washington, D. C.) 2017; 356: eaaf7230

• 6 Kharasch MS, Fuchs CF. J. Am. Chem. Soc. 1943; 65: 504

• 7 Cahiez G, Moyeux A. Chem. Rev. 2010; 110: 1435

• 8 Gosmini C, Moncomble A. Isr. J. Chem. 2010; 50: 568

• 9 Gosmini C, Bégouin J.-M, Moncomble A. Chem. Commun. (Cambridge) 2008; 3221

• 10 Amatore M, Aubert C, Malacria M, Petit M. Science of Synthesis Knowledge Updates 2012; 3: 1

• 11 Guérinot A, Cossy J. Acc. Chem. Res. 2020; 53: 1351

• 12 Röse P, Hilt G. Synthesis 2016; 48: 463

• 13 Rérat A, Gosmini C, In: Grignard Reagents and Transition Metal Catalysts Cossy J. De Gruyter Berlin 2016; 152

• 14 Knappke CEI, Jacobi von Wangelin A. Chem. Soc. Rev. 2011; 40: 4948

• 15 Cahiez G, Moyeux A, Cossy J. Adv. Synth. Catal. 2015; 357: 1983

• 16 Hatakeyama T, Nakamura M. J. Am. Chem. Soc. 2007; 129: 9844

• 17 Hatakeyama T, Hashimoto S, Ishizuka K, Nakamura M. J. Am. Chem. Soc. 2009; 131: 11949

• 18 Wu W, Duong HA. Synlett 2018; 29: 1199

• 19 Malapit CA, Visco MD, Reeves JT, Busacca CA, Howell AR, Senanayake CH. Adv. Synth. Catal. 2015; 357: 2199

• 20 Gülak S, Stepanek O, Malberg J, Rad BR, Kotora M, Wolf R, Jacobi von Wangelin A. Chem. Sci. 2013; 4: 776

• 21 Kuzmina OM, Steib AK, Fernandez S, Boudot W, Markiewicz JT, Knochel P. Chem.–Eur. J. 2015; 21: 8242

• 22 Wakabayashi K, Yorimitsu H, Oshima K. J. Am. Chem. Soc. 2001; 123: 5374

• 23 Ohmiya H, Wakabayashi K, Yorimitsu H, Oshima K. Tetrahedron 2006; 62: 2207

• 24 Ohmiya H, Yorimitsu H, Oshima K. J. Am. Chem. Soc. 2006; 128: 1886

• 25 Cahiez G, Chaboche C, Duplais C, Moyeux A. Org. Lett. 2009; 11: 277

• 26 Nicolas L, Izquierdo E, Angibaud P, Stansfield I, Meerpoel L, Reymond S, Cossy J. J. Org. Chem. 2013; 78: 11807

• 27 Nicolas L, Angibaud P, Stansfield I, Bonnet P, Meerpoel L, Reymond S, Cossy J. Angew. Chem. Int. Ed. 2012; 51: 11101

• 28 Hammann JM, Haas D, Tüllmann C.-P, Karaghiosoff K, Knochel P. Org. Lett. 2016; 18: 4778

• 29 Gonnard L, Guérinot A, Cossy J. Chem.–Eur. J. 2015; 21: 12797

• 30 Barré B, Gonnard L, Campagne R, Reymond S, Marin J, Ciapetti P, Brellier M, Guérinot A, Cossy J. Org. Lett. 2014; 16: 6160

• 31 Barré B, Gonnard L, Guérinot A, Cossy J. Molecules 2018; 23: 1449

• 32 Mao J, Liu F, Wang M, Wu L, Zheng B, Liu S, Zhong J, Bian Q, Walsh PJ. J. Am. Chem. Soc. 2014; 136: 17662

• 33 Zhou Y, Wang L, Yuan G, Liu S, Sun X, Yuan C, Yang Y, Bian Q, Wang M, Zhong J. Org. Lett. 2020; 22: 4532

• 34 Kharasch MS, Lambert FL, Urry WH. J. Org. Chem. 1945; 10: 298

• 35 Cahiez G, Avedissian H. Tetrahedron Lett. 1998; 39: 6159

• 36 Ohmiya H, Yorimitsu H, Oshima K. Chem. Lett. 2004; 33: 1240

• 37 Hamaguchi H, Uemura M, Yasui H, Yorimitsu H, Oshima K. Chem. Lett. 2008; 37: 1178

• 38 Cahiez G, Chaboche C, Duplais C, Giulliani A, Moyeux A. Adv. Synth. Catal. 2008; 350: 1484

• 39 Iwasaki T, Takagawa H, Singh SP, Kuniyasu H, Kambe N. J. Am. Chem. Soc. 2013; 135: 9604

• 40 Iwasaki T, Yamashita K, Kuniyasu H, Kambe N. Org. Lett. 2017; 19: 3691

• 41 Kreyenschmidt F, Koszinowski K. Chem.–Eur. J. 2018; 24: 1168

• 42 Andersen C, Ferey V, Daumas M, Bernardelli P, Guérinot A, Cossy J. Org. Lett. 2019; 21: 2285

• 43 Kuno A, Saino N, Kamachi T, Okamoto S. Tetrahedron Lett. 2006; 47: 2591

• 44 Ohmiya H, Yorimitsu H, Oshima K. Org. Lett. 2006; 8: 3093

• 45 Hsu S.-F, Ko C.-W, Wu Y.-T. Adv. Synth. Catal. 2011; 353: 1756

• 46 Black HK, Horn DHS, Weedon BCL. J. Chem. Soc. 1954; 1704

• 47 Tobisu M, Takahira T, Morioka T, Chatani N. J. Am. Chem. Soc. 2016; 138: 6711

• 48 Li W.-N, Wang Z.-L. RSC Adv. 2013; 3: 25565

• 49 Shirakawa E, Sato T, Imazaki Y, Kimura T, Hayashi T. Chem. Commun. (Cambridge) 2007; 4513

• 50 Shirakawa E, Imazaki Y, Hayashi T. Chem. Lett. 2008; 37: 654

• 51 Piontek A, Ochędzan-Siodłak W, Bisz E, Szostak M. ChemCatChem 2021; 13: 202

• 52 The Chemistry of Organozinc Compounds. Rappoport Z, Marek I. Wiley; New York 2006

• 53 Knochel P. Science of Synthesis 2004; 3: 5

• 54 Dagousset G, François C, León T, Blanc R, Sansiaume-Dagousset E, Knochel P. Synthesis 2014; 46: 3133

• 55 Klatt T, Markiewicz JT, Sämann C, Knochel P. J. Org. Chem. 2014; 79: 4253

• 56 Negishi E, Valente LF, Kobayashi M. J. Am. Chem. Soc. 1980; 102: 3298

• 57 Negishi E. Acc. Chem. Res. 1982; 15: 340

• 58 Metal-Catalyzed Cross-Coupling Reactions. Diederich F, Stang PJ. Wiley-VCH; Weinheim, Germany 1998

• 59 Fürstner A, Leitner A, Méndez M, Krause H. J. Am. Chem. Soc. 2002; 124: 13856

• 60 Bolm C, Legros J, Le Paih J, Zani L. Chem. Rev. 2004; 104: 6217

• 61 Sherry BD, Fürstner A. Acc. Chem. Res. 2008; 41: 1500

• 62 Corpet M, Bai X.-Z, Gosmini C. Adv. Synth. Catal. 2014; 356: 2937

• 63 Hammann JM, Hofmayer MS, Lutter FH, Thomas L, Knochel P. Synthesis 2017; 49: 3887

• 64 Krasovskiy A, Malakhov V, Gavryushin A, Knochel P. Angew. Chem. Int. Ed. 2006; 45: 6040

• 65 Boudet N, Sase S, Sinha P, Liu C.-Y, Krasovskiy A, Knochel P. J. Am. Chem. Soc. 2007; 129: 12358

• 66 Balkenhohl M, Ziegler DS, Desaintjean A, Bole LJ, Kennedy AR, Hevia E, Knochel P. Angew. Chem. Int. Ed. 2019; 58: 12898

• 67 Wang X.-j, Sun X, Zhang L, Xu Y, Krishnamurthy D, Senanayake CH. Org. Lett. 2006; 8: 305

• 68 Fillon H, Gosmini C, Périchon J. J. Am. Chem. Soc. 2003; 125: 3867

• 69 Jin M.-Y, Yoshikai N. J. Org. Chem. 2011; 76: 1972

• 70 Bégouin J.-M, Gosmini C. J. Org. Chem. 2009; 74: 3221

• 71 Amatore M, Gosmini C. Chem. Commun. (Cambridge) 2008; 5019

• 72 Rérat A, Michon C, Agbossou-Niedercorn F, Gosmini C. Eur. J. Org. Chem. 2016; 4554

• 73 Haas D, Hammann JM, Lutter FH, Knochel P. Angew. Chem. Int. Ed. 2016; 55: 3809

• 74 Begouin J.-M, Rivard M, Gosmini C. Chem. Commun. (Cambridge) 2010; 46: 5972

• 75 Hammann JM, Lutter FH, Haas D, Knochel P. Angew. Chem. Int. Ed. 2017; 56: 1082

• 76 Hofmayer MS, Hammann JM, Lutter FH, Knochel P. Synthesis 2017; 49: 3925

• 77 Hernán-Gómez A, Herd E, Hevia E, Kennedy AR, Knochel P, Koszinowski K, Manolikakes SM, Mulvey RE, Schnegelsberg C. Angew. Chem. Int. Ed. 2014; 53: 2706

• 78 Li J, Knochel P. Angew. Chem. Int. Ed. 2018; 57: 11436

• 79 Kremsmair A, Graßl S, Seifert CJB, Godineau E, Knochel P. Synthesis 2021; 53: 4068

• 80 Kazmierski I, Gosmini C, Paris J.-M, Périchon J. Tetrahedron Lett. 2003; 44: 6417

• 81 Kazmierski I, Bastienne M, Gosmini C, Paris J.-M, Périchon J. J. Org. Chem. 2004; 69: 936

• 82 Dorval C, Dubois E, Bourne-Branchu Y, Gosmini C, Danoun G. Adv. Synth. Catal. 2019; 361: 1777

• 83 Lutter FH, Grokenberger L, Hofmayer MS, Knochel P. Chem. Sci. 2019; 10: 8241

• 84 Hammann JM, Haas D, Knochel P. Angew. Chem. Int. Ed. 2015; 54: 4478

• 85 Liu X.-G, Zhou C.-J, Lin E, Han X.-L, Zhang S.-S, Li Q, Wang H. Angew. Chem. Int. Ed. 2018; 57: 13096

• 86 Modern Drug Synthesis. Li JJ, Johnson DS. Wiley; Hoboken, NJ 2010

• 87 Yeh V, Szabo WA, Applications of Transition Metal Catalysis in Drug Discovery and Development: An Industrial Perspective Crawley ML, Trost BM. Wiley Hoboken, NJ 2012; 165

• 88 Haas D, Hammann JM, Greiner R, Knochel P. ACS Catal. 2016; 6: 1540

• 89 Hofmayer MS, Sunagatullina A, Brösamlen D, Mauker P, Knochel P. Org. Lett. 2020; 22: 1286

• 90 Lorion MM, Koch V, Nieger M, Chen H.-Y, Lei A, Bräse S, Cossy J. Chem.–Eur. J. 2020; 26: 13163

• 91 Liu F, Zhong J, Zhou Y, Gao Z, Walsh PJ, Wang X, Ma S, Hou S, Liu S, Wang M, Wang M, Bian Q. Chem.–Eur. J. 2018; 24: 2059

• 92 Weissermel K, Arpe H.-J. Industrial Organic Chemistry. Wiley-VCH; Weinheim, Germany 1997

• 93 Lawrence SA. Amines: Synthesis, Properties and Applications. Cambridge University Press; Cambridge 2004

• 94 Hili R, Yudin AK. Nat. Chem. Biol. 2006; 2: 284

• 95 Teo Y.-C, Chua G.-L. Chem.–Eur. J. 2009; 15: 3072

• 96 Toma G, Fujita K.-i, Yamaguchi R. Eur. J. Org. Chem. 2009; 4586

• 97 Qian X, Yu Z, Auffrant A, Gosmini C. Chem.–Eur. J. 2013; 19: 6225

• 98 Chen Y.-H, Graßl S, Knochel P. Angew. Chem. Int. Ed. 2018; 57: 1108

• 99 Graßl S, Chen Y.-H, Hamze C, Tüllmann CP, Knochel P. Org. Lett. 2019; 21: 494

• 100 Li J, Tan E, Keller N, Chen Y.-H, Zehetmaier PM, Jakowetz AC, Bein T, Knochel P. J. Am. Chem. Soc. 2019; 141: 98

• 101 Graßl S, Knochel P. Org. Lett. 2020; 22: 1947

• 102 Reddy CK, Knochel P. Angew. Chem. Int. Ed. Engl. 1996; 35: 1700

• 103 Avedissian H, Bérillon L, Cahiez G, Knochel P. Tetrahedron Lett. 1998; 39: 6163

• 104 Metzger A, Schade MA, Knochel P. Org. Lett. 2008; 10: 1107

• 105 Metzger A, Schade MA, Manolikakes G, Knochel P. Asian J. Chem. 2008; 3: 1678

• 106 Metzger A, Piller FM, Knochel P. Chem. Commun. (Cambridge) 2008; 5824

• 107 Benischke AD, Knoll I, Rérat A, Gosmini C, Knochel P. Chem. Commun. (Cambridge) 2016; 52: 3171

• 108 Bégouin JM, Claudel S, Gosmini C. Synlett 2009; 3192

• 109 Baumann M, Baxendale IR. Beilstein J. Org. Chem. 2013; 9: 2265

• 110 Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257

• 111 Lutter FH, Grokenberger L, Spieß P, Hammann JM, Karaghiosoff K, Knochel P. Angew. Chem. Int. Ed. 2020; 59: 5546

• 112 Zhang X, McNally A. ACS Catal. 2019; 9: 4862

• 113 Cárdenas DJ. Angew. Chem. Int. Ed. 2003; 42: 384

• 114 Lutter FH, Grokenberger L, Benz M, Knochel P. Org. Lett. 2020; 22: 3028

• 115 Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis. Christoffers J, Baro A. Wiley-VCH; Weinheim, Germany 2005

• 116 Quasdorf KW, Overman LE. Nature (London) 2014; 516: 181

• 117 Palao E, López E, Torres-Moya I, de la Hoz A, Díaz-Ortiz Á, Alcázar J. Chem. Commun. (Cambridge) 2020; 56: 8210

• 118 Dilauro G, Messa F, Bona F, Perrone S, Salomone A. Chem. Commun. (Cambridge) 2021; 57: 10564

• 119 Neely JM, Bezdek MJ, Chirik PJ. ACS Cent. Sci. 2016; 2: 935

• 120 Kumar LM, Bhat BR. J. Organomet. Chem. 2017; 827: 41

• 121 Duong HA, Wu W, Teo Y.-Y. Organometallics 2017; 36: 4363

• 122 Asghar S, Tailor SB, Elorriaga D, Bedford RB. Angew. Chem. Int. Ed. 2017; 56: 16367

• 123 Tailor SB, Manzotti M, Smith GJ, Davis SA, Bedford RB. ACS Catal. 2021; 11: 3856

• 124 Ludwig JR, Simmons EM, Wisniewski SR, Chirik PJ. Org. Lett. 2021; 23: 625

• 125 Mills LR, Gygi D, Ludwig JR, Simmons EM, Wisniewski SR, Kim J, Chirik PJ. ACS Catal. 2022; 12: 1905

• 126 Hofmayer MS, Hammann JM, Haas D, Knochel P. Org. Lett. 2016; 18: 6456

• 127 Korn TJ, Knochel P. Angew. Chem. Int. Ed. 2005; 44: 2947

• 128 Miyaura N, Buchwald SL. Top. Curr. Chem. 2002; 219

• 129 Komiyama T, Minami Y, Hiyama T. ACS Catal. 2017; 7: 631

• 130 Zhang Y.-F, Shi Z.-J. Acc. Chem. Res. 2019; 52: 161

• 131 Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417

• 132 Amatore M, Gosmini C. Chem.–Eur. J. 2010; 16: 5848

• 133 Knappke CEI, Grupe S, Gärtner D, Corpet M, Gosmini C, Jacobi von Wangelin A. Chem.–Eur. J. 2014; 20: 6828

• 134 Amatore M, Gosmini C. Angew. Chem. Int. Ed. 2008; 47: 2089

• 135 Pal S, Chowdhury S, Rozwadowski E, Auffrant A, Gosmini C. Adv. Synth. Catal. 2016; 358: 2431

• 136 Cai Y, Benischke AD, Knochel P, Gosmini C. Chem.–Eur. J. 2017; 23: 250

• 137 Czaplik WM, Mayer M, Jacobi von Wangelin A. Synlett 2009; 2931

• 138 Yu D.-G, Li B.-J, Shi Z.-J. Acc. Chem. Res. 2010; 43: 1486

• 139 Gomes P, Gosmini C, Périchon J. Org. Lett. 2003; 5: 1043

• 140 Reddy BRP, Chowdhury S, Auffrant A, Gosmini C. Adv. Synth. Catal. 2018; 360: 3026

• 141 Amatore M, Gosmini C, Périchon J. Eur. J. Org. Chem. 2005; 989

• 142 Gomes P, Gosmini C, Périchon J. Tetrahedron 2003; 59: 2999

• 143 Tsuji T, Yorimitsu H, Oshima K. Angew. Chem. Int. Ed. 2002; 41: 4137

• 144 Ohmiya H, Tsuji T, Yorimitsu H, Oshima K. Chem.–Eur. J. 2004; 10: 5640

• 145 Qian X, Auffrant A, Felouat A, Gosmini C. Angew. Chem. Int. Ed. 2011; 50: 10402

• 146 Ma W.-Y, Han G.-Y, Kang S, Pang X, Liu X.-Y, Shu X.-Z. J. Am. Chem. Soc. 2021; 143: 15930

• 147 Song F, Gou T, Wang B.-Q, Shi Z.-J. Chem. Soc. Rev. 2018; 47: 7078

• 148 Lutz MDR, Morandi B. Chem. Rev. 2021; 121: 300

• 149 Souillart L, Cramer N. Chem. Rev. 2015; 115: 9410

• 150 Nakao Y. Chem. Rev. 2021; 121: 327

• 151 Dorval C, Tricoire M, Bégouin J.-M, Gandon V, Gosmini C. ACS Catal. 2020; 10: 12819

• 152 Shu T, Cossy J. Chem.–Eur. J. 2021; 27: 11021