1.15 Nickel-Catalyzed Nondirected C—H Functionalization

Abstract

This chapter summarizes some selected examples of nickel-catalyzed nondirected C—H functionalization reactions. Nickel(0) complexes have been demonstrated to be effective for C—H alkylation and alkenylation reactions of arenes and hetarenes through a ligand-to-ligand hydrogen-transfer mechanism for C—H activation that is unique to nickel-catalyzed approaches. They also effect the C—H borylation of arenes and hetarenes. Some nickel(II) complexes are shown to catalyze cross-coupling-type transformations of hetarenes with organic electrophiles through C—H activation by nickel(II) intermediates.

Schlüsselwörter

base-metal catalysis - C—H activation - C—H alkylation - C—H alkenylation - C—H arylation - C—H alkynylation - C—H borylation - C—H functionalization - nickel catalysis

• 1 Kleiman JP, Dubeck M. J. Am. Chem. Soc. 1963; 85: 1544

• 2 Khake SM, Chatani N. Chem 2020; 6: 1056

• 3 Khake SM, Chatani N. Trends Chem. 2019; 1: 524

• 4 Nakao Y. Science of Synthesis: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 2016; 1: 425

• 5 Nakao Y. Science of Synthesis: Catalytic Transformations via C—H Activation 2015; 1: 299

• 6 Vechorkin O, Proust V, Hu X. Angew. Chem. Int. Ed. 2010; 49: 3061

• 7 Yao T, Hirano K, Satoh T, Miura M. Chem.–Eur. J. 2010; 16: 12307

• 8 Ackermann L, Punji B, Song W. Adv. Synth. Catal. 2011; 353: 3325

• 9 Xin P.-Y, Niu H.-Y, Qu G.-R, Ding R.-F, Guo H.-M. Chem. Commun. (Cambridge) 2012; 48: 6717

• 10 Saper NI, Ohgi A, Small DW, Semba K, Nakao Y, Hartwig JF. Nat. Chem. 2020; 12: 276

• 11 Nakao Y, Kashihara N, Kanyiva KS, Hiyama T. J. Am. Chem. Soc. 2008; 130: 16170

• 12 Bair JS, Schramm Y, Sergeev AG, Clot E, Eisenstein O, Hartwig JF. J. Am. Chem. Soc. 2014; 136: 13098

• 13 Okumura S, Tang S, Saito T, Semba K, Sakaki S, Nakao Y. J. Am. Chem. Soc. 2016; 138: 14699

• 14 Okumura S, Ebara T, Semba K, Nakao Y. Heterocycles 2019; 99: 1128

• 15 Okumura S, Nakao Y. Org. Lett. 2017; 19: 584

• 16 Okumura S, Komine T, Shigeki E, Semba K, Nakao Y. Angew. Chem. Int. Ed. 2018; 57: 929

• 17 Schramm Y, Takeuchi M, Semba K, Nakao Y, Hartwig JF. J. Am. Chem. Soc. 2015; 137: 12215

• 18 Nakao Y, Kashihara N, Kanyiva KS, Hiyama T. Angew. Chem. Int. Ed. 2010; 49: 4451

• 19 Jiang Y.-Y, Li Z, Shi J. Organometallics 2012; 31: 4356

• 20 Shih W.-C, Chen W.-C, Lai Y.-C, Yu M.-S, Ho J.-J, Yap GPA, Ong T.-G. Org. Lett. 2012; 14: 2046

• 21 Lee W.-C, Wang C.-H, Lin Y.-H, Shih W.-C, Ong T.-G. Org. Lett. 2013; 15: 5358

• 22 Normand AT, Yen SK, Huynh HV, Hor TSA, Cavell KJ. Organometallics 2008; 27: 3153

• 23 Wang Y.-X, Qi S.-L, Luan Y.-X, Han X.-W, Wang S, Chen H, Ye M. J. Am. Chem. Soc. 2018; 140: 5360

• 24 Loup J, Müller V, Ghorai D, Ackermann L. Angew. Chem. Int. Ed. 2019; 58: 1749

• 25 Nakao Y, Yamada Y, Kashihara N, Hiyama T. J. Am. Chem. Soc. 2010; 132: 13666

• 26 Yu M.-S, Lee W.-C, Chen C.-H, Tsai F.-Y, Ong T.-G. Org. Lett. 2014; 16: 4826

• 27 Zhang W.-B, Yang X.-T, Ma J.-B, Su Z.-M, Shi S.-L. J. Am. Chem. Soc. 2019; 141: 5628

• 28 Tamura R, Yamada Y, Nakao Y, Hiyama T. Angew. Chem. Int. Ed. 2012; 51: 5679

• 29 Donets PA, Cramer N. Angew. Chem. Int. Ed. 2015; 54: 633

• 30 Diesel J, Finogenova AM, Cramer N. J. Am. Chem. Soc. 2018; 140: 4489

• 31 Yao T, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2012; 51: 775

• 32 Meng L, Kamada Y, Muto K, Yamaguchi J, Itami K. Angew. Chem. Int. Ed. 2013; 52: 10048

• 33 Muto K, Hatakeyama T, Yamaguchi J, Itami K. Chem. Sci. 2015; 6: 6792

• 34 Kanyiva KS, Löbermann F, Nakao Y, Hiyama T. Tetrahedron Lett. 2009; 50: 3463

• 35 Nakao Y, Kanyiva KS, Oda S, Hiyama T. J. Am. Chem. Soc. 2006; 128: 8146

• 36 Kanyiva KS, Nakao Y, Hiyama T. Heterocycles 2007; 72: 677

• 37 Nett AJ, Zhao W, Zimmerman PM, Montgomery J. J. Am. Chem. Soc. 2015; 137: 7636

• 38 Nakao Y, Kanyiva KS, Hiyama T. J. Am. Chem. Soc. 2008; 130: 2448

• 39 Tsai C.-C, Shih W.-C, Fang C.-H, Li C.-Y, Ong T.-G, Yap GPA. J. Am. Chem. Soc. 2010; 132: 11887

• 40 Zhang T, Luan Y.-X, Lam NYS, Li J.-F, Li Y, Ye M, Yu J.-Q. Nat. Chem. 2021; 13: 1207

• 41 Kanyiva KS, Nakao Y, Hiyama T. Angew. Chem. Int. Ed. 2007; 46: 8872

• 42 Nakao Y, Idei H, Kanyiva KS, Hiyama T. J. Am. Chem. Soc. 2009; 131: 15996

• 43 Yin G, Li Y, Wang R.-H, Li J.-F, Xu X.-T, Luan Y.-X, Ye M. ACS Catal. 2021; 11: 4606

• 44 Hachiya H, Hirano K, Satoh T, Miura M. Org. Lett. 2009; 11: 1737

• 45 Yamamoto T, Muto K, Komiyama M, Canivet J, Yamaguchi J, Itami K. Chem.–Eur. J. 2011; 17: 10113

• 46 Muto K, Yamaguchi J, Itami K. J. Am. Chem. Soc. 2012; 134: 169

• 47 Amaike K, Muto K, Yamaguchi J, Itami K. J. Am. Chem. Soc. 2012; 134: 13573

• 48 Lapointe D, Fagnou K. Chem. Lett. 2010; 39: 1118

• 49 Muto K, Yamaguchi J, Lei A, Itami K. J. Am. Chem. Soc. 2013; 135: 16384

• 50 Xu H, Muto K, Yamaguchi J, Zhao C, Itami K, Musaev DG. J. Am. Chem. Soc. 2014; 136: 14834

• 51 Yin Y, Yue X, Zhong Q, Jiang H, Bai R, Lan Y, Zhang H. Adv. Synth. Catal. 2018; 360: 1639

• 52 Wang T.-H, Ambre R, Wang Q, Lee W.-C, Wang P.-C, Liu Y, Zhao L, Ong T.-G. ACS Catal. 2018; 8: 11368

• 53 Yang K, Wang P, Zhang C, Kadi AA, Fun H.-K, Zhang Y, Lu H. Eur. J. Org. Chem. 2014; 7586

• 54 Qu G.-R, Xin P.-Y, Niu H.-Y, Wang D.-C, Ding R.-F, Guo H.-M. Chem. Commun. (Cambridge) 2011; 47: 11140

• 55 Tobisu M, Hyodo I, Chatani N. J. Am. Chem. Soc. 2009; 131: 12070

• 56 Matsuyama N, Hirano K, Satoh T, Miura M. Org. Lett. 2009; 11: 4156

• 57 Patel UN, Punji B. Asian J. Org. Chem. 2018; 7: 1390

• 58 Matsuyama N, Kitahara M, Hirano K, Satoh T, Miura M. Org. Lett. 2010; 12: 2358

• 59 Mkhalid IAI, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem. Rev. 2010; 110: 890

• 60 Furukawa T, Tobisu M, Chatani N. Chem. Commun. (Cambridge) 2015; 51: 6508

• 61 Zhang H, Hagihara S, Itami K. Chem. Lett. 2015; 44: 779