Recent Advances in Palladium-Catalyzed C(sp³)–H Activation for the Formation of Carbon–Carbon and Carbon–Heteroatom Bonds

Abstract

Within this review, recent developments in the field of C(sp³)–H activation catalyzed by palladium are discussed. Both intra­- and intermolecular reactions towards carbon–carbon and carbon–heteroatom bonds are covered. In the case of intramolecular reactions­, asymmetric versions are reported as well. The main focus of this review is literature of the last five years until late 2013.

1 Introduction

2 Intramolecular C(sp³)–H Activation

2.1 Carbon–Carbon Coupling

2.2 Carbon–Heteroatom Coupling

2.3 Stereoselective Reactions

3 Intermolecular C(sp³)–H Activation

3.1 Carbon–Carbon Coupling

3.2 Carbon–Heteroatom Coupling

4 Conclusion and Outlook

Key words

alkylation - arylation - palladacycles - homogeneous catalysis - organometallic reagents

• References


For recent reviews on various aspects of C–H activation, see:
• 1a Roquet G, Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11726
• 1b Peng B, Maulide N. Chem. Eur. J. 2013; 19: 13274
• 1c Thirunavukkarasu VS, Kozhushkov SI, Ackermann L. Chem. Commun. 2014; 50: 29
• 1d Patureau FW, Wencel-Delord J, Glorius F. Aldrichimica Acta 2012; 45: 31
• 1e Arockiam PB, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879
• 1f Wencel-Delord J, Glorius F. Nature Chem. 2013; 5: 369

For reviews dedicated to sp² C–H activation, see:
• 2a Li B, Dixneuf PH. Chem. Soc. Rev. 2013; 42: 5744
• 2b Engle KM, Yu J.-Q. J. Org. Chem. 2013; 78: 8927
• 2c Kozhushkov SI, Ackermann L. Chem. Sci. 2013; 4: 886
• 2d Mousseau JJ, Charette AB. Acc. Chem. Res. 2012; 46: 412
• 2e Neufeldt SR, Sanford MS. Acc. Chem. Res. 2012; 45: 936

For reviews on sp³ C–H activation, see:
• 3a Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
• 3b Ramirez TA, Zhao B, Shi Y. Chem. Soc. Rev. 2012; 41: 931
• 3c Zhang S.-Y, Zhang F.-M, Tu Y.-Q. Chem. Soc. Rev. 2011; 40: 1937
• 3d Mei T.-S, Kou L, Ma S, Engle KM, Yu J.-Q. Synthesis 2012; 44: 1778
• 4 Li H, Li B.-J, Shi Z.-J. Catal. Sci. Technol. 2011; 1: 191
• 5 Dyker G. Angew. Chem. Int. Ed. 1992; 31: 1023
• 6 Dyker G. Angew. Chem. Int. Ed. 1994; 33: 103
• 7 Baudoin O, Herrbach A, Gueritte F. Angew. Chem. Int. Ed. 2003; 42: 5736
• 8 Lafrance M, Gorelsky SI, Fagnou K. J. Am. Chem. Soc. 2007; 129: 14570
• 9 Watanabe T, Oishi S, Fujii N, Ohno H. Org. Lett. 2008; 10: 1759
• 10 Liegault B, Fagnou K. Organometallics 2008; 27: 4841
• 11 Rousseaux S, Gorelsky SI, Chung BK. W, Fagnou K. J. Am. Chem. Soc. 2010; 132: 10692
• 12 Liang Y, Geng W, Wei J, Ouyang K, Xi Z. Org. Biomol. Chem. 2012; 10: 1537
• 13 Hsiao C.-C, Lin Y.-K, Liu C.-J, Wu T.-C, Wu Y.-T. Adv. Synth. Catal. 2010; 352: 3267
• 14 Pierre C, Baudoin O. Org. Lett. 2011; 13: 1816
• 15 Guyonnet M, Baudoin O. Org. Lett. 2012; 14: 398
• 16 Sofack-Kreutzer J, Martin N, Renaudat A, Jazzar R, Baudoin O. Angew. Chem. Int. Ed. 2012; 51: 10399
• 17 Rousseaux S, Liegault B, Fagnou K. Chem. Sci. 2012; 3: 244
• 18 Saget T, Perez D, Cramer N. Org. Lett. 2013; 15: 1354
• 19 Ladd CL, Sustac Roman D, Charette AB. Org. Lett. 2013; 15: 1350
• 20 Feng Y, Wang Y, Landgraf B, Liu S, Chen G. Org. Lett. 2010; 12: 3414
• 21 Shi Z, Suri M, Glorius F. Angew. Chem. Int. Ed. 2013; 52: 4892
• 22 Tsukano C, Okuno M, Takemoto Y. Angew. Chem. Int. Ed. 2012; 51: 2763
• 23 Zhang Q, Yu H.-Z, Fu Y. Organometallics 2013; 32: 4165
• 24 Tsukano C, Okuno M, Takemoto Y. Chem. Lett. 2013; 42: 753
• 25 Nanjo T, Tsukano C, Takemoto Y. Org. Lett. 2012; 14: 4270
• 26 Piou T, Neuville L, Zhu J. Angew. Chem. Int. Ed. 2012; 51: 11561
• 27a Jones WD. Acc. Chem. Res. 2003; 36: 140
• 27b Dastbaravardeh N, Kirchner K, Schnürch M, Mihovilovic MD. J. Org. Chem. 2013; 78: 658
• 28 Simmons EM, Hartwig JF. Angew. Chem. Int. Ed. 2012; 51: 3066
• 29 Piou T, Bunescu A, Wang Q, Neuville L, Zhu J. Angew. Chem. Int. Ed. 2013; 52: 12385
• 30 Dong C.-G, Hu Q.-S. Angew. Chem. Int. Ed. 2006; 45: 2289
• 31 Liu T.-P, Xing C.-H, Hu Q.-S. Angew. Chem. Int. Ed. 2010; 49: 2909
• 32 Dong C.-G, Hu Q.-S. Tetrahedron 2008; 64: 2537
• 33 Xie H, Zhang H, Lin Z. New J. Chem. 2013; 37: 2856
• 34 Ren H, Li Z, Knochel P. Chem. Asian J. 2007; 2: 416
• 35 Neumann JJ, Rakshit S, Droege T, Glorius F. Angew. Chem. Int. Ed. 2009; 48: 6892
• 36 He G, Zhao Y, Zhang S, Lu C, Chen G. J. Am. Chem. Soc. 2012; 134: 3
• 37 Novak P, Correa A, Gallardo-Donaire J, Martin R. Angew. Chem. Int. Ed. 2011; 50: 12236
• 38 Hartwig JF. Inorg. Chem. 2007; 46: 1936
• 39 Eom D, Jeong Y, Kim YR, Lee E, Choi W, Lee PH. Org. Lett. 2013; 15: 5210
• 40 Kündig EP, Seidel TM, Jia Y.-x, Bernardinelli G. Angew. Chem. Int. Ed. 2007; 46: 8484
• 41 Nakanishi M, Katayev D, Besnard C, Kündig EP. Angew. Chem. Int. Ed. 2011; 50: 7438
• 42 Larionov E, Nakanishi M, Katayev D, Besnard C, Kündig EP. Chem. Sci. 2013; 4: 1995
• 43 Anas S, Cordi A, Kagan HB. Chem. Commun. 2011; 47: 11483
• 44 Martin N, Pierre C, Davi M, Jazzar R, Baudoin O. Chem. Eur. J. 2012; 18: 4480
• 45 Saget T, Lemouzy SJ, Cramer N. Angew. Chem. Int. Ed. 2012; 51: 2238
• 46 Saget T, Cramer N. Angew. Chem. Int. Ed. 2012; 51: 12842
• 47 Zaitsev VG, Shabashov D, Daugulis O. J. Am. Chem. Soc. 2005; 127: 13154
• 48a Daugulis O, Zaitsev VG. Angew. Chem. Int. Ed. 2005; 44: 4046
• 48b Shabashov D, Daugulis O. Org. Lett. 2005; 7: 3657
• 49 Shabashov D, Daugulis O. J. Am. Chem. Soc. 2010; 132: 3965
• 50 Pan F, Shen P.-X, Zhang L.-S, Wang X, Shi Z.-J. Org. Lett. 2013; 15: 4758
• 51 Chen K, Hu F, Zhang S.-Q, Shi B.-F. Chem. Sci. 2013; 4: 3906

For examples, see:
• 52a Matsumura D, Kitazawa K, Terai S, Kochi T, Ie Y, Nitani M, Aso Y, Kakiuchi F. Org. Lett. 2012; 14: 3882
• 52b Martinez R, Simon M.-O, Chevalier R, Pautigny C, Genêt J.-P, Darses S. J. Am. Chem. Soc. 2009; 131: 7887
• 52c Preston AJ, Hofacker AL, Parquette JR. Chemtracts 2002; 15: 623
• 52d Lim Y.-G, Kang J.-B, Kim YH. J. Chem. Soc., Perkin Trans. 1 1996; 17: 2201
• 53 Zheng B, Jia T, Walsh PJ. Org. Lett. 2013; 15: 4190
• 54a Lee HW, Lam FL, So CM, Lau CP, Chan AS. C, Kwong FY. Angew. Chem. Int. Ed. 2009; 48: 7436
• 54b So CM, Lau CP, Kwong FY. Org. Lett. 2007; 9: 2795
• 55 Xie P, Xia C, Huang H. Org. Lett. 2013; 15: 3370
• 56 Xie P, Xie Y, Qian B, Zhou H, Xia C, Huang H. J. Am. Chem. Soc. 2012; 134: 9902
• 57a Jana KJ, Grimme S, Studer A. Chem. Eur. J. 2009; 15: 9078
• 57b Prokopcova H, Bergman SD, Aelvoet K, Smout V, Herrebout W, Van der Veken B, Meerpoel L, Maes BU. W. Chem. Eur. J. 2010; 16: 13063
• 57c Smout V, Peschiulli A, Verbeeck S, Herrebout W, Bultinck P, Vande Velde CM. L, Berthelot D, Meerpoel L, Maes BU. W. J. Org. Chem. 2013; 78: 9803
• 57d Dastbaravardeh N, Schnürch M, Mihovilovic MD. Org. Lett. 2012; 14: 1930
• 58 Giri R, Maugel N, Li J.-J, Wang D.-H, Breazzano SP, Saunders LB, Yu J.-Q. J. Am. Chem. Soc. 2007; 129: 3510
• 59 Chen X, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 12634
• 60 Wang D.-H, Wasa M, Giri R, Yu J.-Q. J. Am. Chem. Soc. 2008; 130: 7190
• 61 Wasa M, Engle KM, Yu J.-Q. J. Am. Chem. Soc. 2009; 131: 9886
• 62 Figg TM, Wasa M, Yu J.-Q, Musaev DG. J. Am. Chem. Soc. 2013; 135: 14206
• 63 Wasa M, Chan KS. L, Zhang X.-G, He J, Miura M, Yu J.-Q. J. Am. Chem. Soc. 2012; 134: 18570
• 64 He J, Wasa M, Chan KS. L, Yu J.-Q. J. Am. Chem. Soc. 2013; 135: 3387
• 65 Parella R, Gopalakrishnan B, Babu SA. Org. Lett. 2013; 15: 3238
• 66 Zhang J, Bellomo A, Creamer AD, Dreher SD, Walsh PJ. J. Am. Chem. Soc. 2012; 134: 13765
• 67a Dreher SD, Dormer PG, Sandrock DL, Molander GA. J. Am. Chem. Soc. 2008; 130: 9257
• 67b Dreher SD, Lim SE, Sandrock DL, Molander GA. J. Org. Chem. 2009; 74: 3626
• 67c Molander GA, Argintaru OA, Aron I, Dreher SD. Org. Lett. 2010; 12: 5783
• 67d Molander GA, Trice SL. J, Dreher SD. J. Am. Chem. Soc. 2010; 132: 17701
• 67e Sandrock DL, Jean-Gerard L, Chen CY, Dreher SD, Molander GA. J. Am. Chem. Soc. 2010; 132: 17108
• 68 Wang G.-W, Zhou A.-X, Wang J.-J, Hu R.-B, Yang S.-D. Org. Lett. 2013; 15: 5270
• 69a Baumann M, Baxendale IR, Ley SV, Nikbin N. Beilstein J. Org. Chem. 2011; 7: 442
• 69b Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry and Biochemistry and the Role of Heterocycles in Science, Technology, Medicine, and Agriculture. Pozharsky AF, Soldatenkov AT, Katritzky AR. John Wiley and Sons; Chichester: 1997
• 69c Bellus D. Lect. Heterocycl. Chem. 1987; 9: 65
• 69d Muller T, Braese S. Angew. Chem. Int. Ed. 2011; 50: 11844
• 69e Rasmussen SC, Schwiderski RL, Mulholland ME. Chem. Commun. 2011; 47: 11394
• 69f Maly KE. J. Mat. Chem. 2009; 19: 1781
• 69g Elbing M, Bazan GC. Angew. Chem. Int. Ed. 2008; 47: 834
• 70 Thu H.-Y, Yu W.-Y, Che C.-M. J. Am. Chem. Soc. 2006; 128: 9048
• 71 Stowers KJ, Kubota A, Sanford MS. Chem. Sci. 2012; 3: 3192
• 72 Ren Z, Mo F, Dong G. J. Am. Chem. Soc. 2012; 134: 16991
• 73 Kubota A, Sanford MS. Synthesis 2011; 2579
• 74 Zhao D, Zhu M.-X, Wang Y, Shen Q, Li J.-X. Org. Biomol. Chem. 2013; 11: 6246
• 75 Iglesias A, Álvarez R, de Lera AR, Muñiz K. Angew. Chem. Int. Ed. 2012; 51: 2225
• 76 Baudoux J, Cahard D. Org. React. (N. Y.) 2007; 69: 347
• 77 Wang D.-H, Hao X.-S, Wu D.-F, Yu J.-Q. Org. Lett. 2006; 8: 3387
• 78 Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 10236