Advances in Transition-Metal-Catalyzed Direct sp3-Carbon–Hydrogen Bond Functionalization

Wei Zhang; Nai-Xing Wang; Yalan Xing

doi:10.1055/s-0034-1381031

Synlett, Table of Contents

Synlett 2015; 26(15): 2088-2098
DOI: 10.1055/s-0034-1381031

account

Advances in Transition-Metal-Catalyzed Direct sp³-Carbon–Hydrogen Bond Functionalization

Wei Zhang

^aTechnical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China Email: nxwang@mail.ipc.ac.cn

,

Nai-Xing Wang*

^aTechnical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China Email: nxwang@mail.ipc.ac.cn

,

Yalan Xing*

^bDepartment of Chemistry, William Paterson University of New Jersey, 300 Pompton Road, Wayne NJ 07470, USA Email: xingy@wpunj.edu

› Author Affiliations

Abstract

All articles of this category

Abstract

Transition-metal-catalyzed direct carbon–hydrogen bond functionalization has made significant advances in the field of carbon–hydrogen bond activation over the past decades. This methodology has the potential to be used in many different areas of chemistry; for example, it can provide an opportunity for the synthesis of various kinds of complex compounds. This account mainly focuses on recent advances in transition-metal-catalyzed direct sp³-carbon–hydrogen bond functionalization to form carbon–carbon bonds.

1 Introduction

2 Carbon–Carbon Bond Formation via Direct sp³-Carbon–Hydrogen Bond Functionalization

2.1 Coupling of sp³-Carbon–Hydrogen and sp-Carbon–Hydrogen Bonds

2.2 Coupling of sp³-Carbon–Hydrogen and sp²-Carbon–Hydrogen Bonds

2.3 Coupling of sp³-Carbon–Hydrogen and sp³-Carbon–Hydrogen Bonds

2.4 Coupling of sp³-Carbon–Hydrogen and C–X Bonds

3 Conclusion

Key words

transition metals - catalysis - carbon–carbon bond formations - cross-dehydrogenative coupling - direct bond functionalizations

Full Text

References

References

For selected examples, see:

1a Ackermann L, Vicente R, Kapdi A. Angew. Chem. Int. Ed. 2009; 48: 9792
1b Wencel-Delord J, Dröge T, Liu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740
1c Cho SH, Kim JY, Kwak J, Chang S. Chem. Soc. Rev. 2011; 40: 5068
1d Deng Y, Persson A, Backvall J.-E. Chem. Eur. J. 2012; 18: 11498
1e Song W, Kozhushkov S, Achermann L. Angew. Chem. Int. Ed. 2013; 52: 6576
1f Ackermann L. Chem. Rev. 2011; 111: 1315
1g Ackermann L. Acc. Chem. Res. 2014; 47: 281
1h Arnold PL, McMullon MW, Rieb J, Kuhn FE. Angew. Chem. Int. Ed. 2015; 54: 82
1i Chen DY, Youn SW. Chem. Eur. J. 2012; 18: 9452
1j Chu X.-Q, Meng H, Zi Y, Xu X.-P, Ji S.-J. Org. Chem. Front. 2015; 2: 216
1k Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
1l Colby DA, Tsai AS, Bergman RG, Ellman JA. Acc. Chem. Res. 2012; 45: 814
1m Shang X, Liu ZQ. Chem. Soc. Rev. 2013; 42: 3253
1n Zhang SY, Zhang FM, Tu YQ. Chem. Soc. Rev. 2011; 40: 1937

2a Gaich T, Baran PS. J. Org. Chem. 2010; 75: 4657
2b Newhouse T, Baran PS, Hoffmann RW. Chem. Soc. Rev. 2009; 38: 3010

3a Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
3b Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
3c Li B.-J, Shi Z.-J. Chem. Soc. Rev. 2012; 41: 5588
3d See also ref. 3d.
3e Louillat M.-L, Patureau FW. Chem. Rev. 2014; 43: 901
3f Girard SA, Knauber T, Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74

4 Li C.-J. Acc. Chem. Res. 2009; 42: 335

5a Kozhushkov SI, Ackermann L. Chem. Sci. 2013; 4: 886
5b See also ref. 5m.
5c Patureau FW, Wencel-Delord J, Glorius F. Aldrichimica Acta 2012; 45: 31
5d Hirano K, Miura M. Chem. Commun. 2012; 48: 10704
5e Yang L, Huang H. Catal. Sci. Technol. 2012; 2: 1099
5f Sun C.-L, Li B.-J, Shi Z.-J. Chem. Rev. 2011; 111: 1293
5g Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
5h See also ref. 1c.
5i Klussmann M, Sureshkumar D. Synthesis 2011; 353
5j Liu C, Zhang H, Shi W, Lei A. Chem. Rev. 2011; 111: 1780
5k Li C.-J, Li Z. Pure Appl. Chem. 2006; 78: 935
5l Sarhan AA. O, Bolm C. Chem. Soc. Rev. 2009; 38: 2730
5m Scheuermann CJ. Chem. Asian J. 2010; 5: 436
5n Ashenhurst JA. Chem. Soc. Rev. 2010; 39: 540

6 Li Z, Li C.-J. J. Am. Chem. Soc. 2004; 126: 11810

7a Li Z, Li C.-J. Org. Lett. 2004; 6: 4997
7b Li Z, MacLeod PD, Li C.-J. Tetrahedron: Asymmetry 2006; 17: 590

8 Su W, Yu J, Li Z, Jiang Z. J. Org. Chem. 2011; 76: 9144
9 Yu J, Li Z, Jia K, Jiang Z, Liu M, Su W. Tetrahedron Lett. 2013; 54: 2006
10 Zhao L, Li C.-J. Angew. Chem. Int. Ed. 2008; 47: 7075
11 Correia CA, Li C.-J. Heterocycles 2010; 82: 555
12 Correia CA, Li C.-J. Adv. Synth. Catal. 2010; 352: 1446
13 Sugiishi T, Nakamura H. J. Am. Chem. Soc. 2012; 134: 2504
14 Ma Y, Zhang S, Yang S, Song F, You J. Angew. Chem. Int. Ed. 2014; 53: 7870
15 Nakai K, Yoshida Y, Kurahashi T, Matsubara S. J. Am. Chem. Soc. 2014; 136: 7797
16 Kim S, Hong SH. Adv. Synth. Catal. 2015; 357: 1004
17 Liang T, Nguyen KD, Zhang W, Krische MJ. J. Am. Chem. Soc. 2015; 137: 3161
18 Moran-Poladura P, Rubio E, Gonzalez JM. Angew. Chem. Int. Ed. 2015; 54: 3052
19 Li Z, Li C.-J. J. Am. Chem. Soc. 2005; 127: 6968
20 Deng G, Zhao L, Li C.-J. Angew. Chem. Int. Ed. 2008; 47: 6278
21 Guo X, Li C.-J. Org. Lett. 2011; 13: 4977
22 Deboef B, Pastine SJ, Sames D. J. Am. Chem. Soc. 2004; 126: 6556

23a Li B, Fagnou K. Organometallics 2008; 27: 4841
23b Wasa M, Engle KM, Yu J.-Q. J. Am. Chem. Soc. 2010; 132: 3680
23c Stowers KJ, Fortner KC, Sanford MS. J. Am. Chem. Soc. 2011; 133: 6541

24 Wu T, Mu X, Liu G. Angew. Chem. Int. Ed. 2011; 50: 12578
25 Yip K.-T, Nimje RY, Leskinen MV, Pihko PM. Chem. Eur. J. 2012; 18: 12590
26 Zhu W, Zhang D, Yang N, Liu H. Chem. Commun. 2014; 50: 10634
27 Aihara Y, Tobisu M, Fukumoto Y, Chatani N. J. Am. Chem. Soc. 2014; 136: 15509
28 Zhang JX, Wang YJ, Zhang W, Wang NX, Bai CB, Xing YL, Li YH, Wen JL. Sci. Rep. 2014; 4: 7446
29 Zhang JX, Wang YJ, Wang NX, Zhang W, Bai CB, Li YH, Wen JL. Synlett 2014; 25: 1621
30 Cheng JK, Loh TP. J. Am. Chem. Soc. 2015; 137: 42
31 Guo S, Li Y, Wang Y, Guo X, Meng X, Chen B. Adv. Synth. Catal. 2015; 357: 950
32 Li Z, Li C.-J. J. Am. Chem. Soc. 2005; 127: 3672
33 Basl O, Li C.-J. Green Chem. 2007; 9: 1047

34a Ishii Y, Sakaguchi S, Iwahama T. Adv. Synth. Catal. 2001; 343: 393
34b Galli C, Gentili P, Lanzalunga O. Angew. Chem. Int. Ed. 2008; 47: 4790

35 Zhang Y, Li C.-J. Eur. J. Org. Chem. 2007; 4654
36 Mao S, Gao Y.-R, Zhang S.-L, Guo D.-D, Wang Y.-Q. Eur. J. Org. Chem. 2015; 876
37 Yang K, Song Q. Org. Lett. 2015; 17: 548
38 Zaitsev VG, Shabashov D, Daugulis O. J. Am. Chem. Soc. 2005; 127: 13154
39 Wei Y, Tang H, Cong X, Rao B, Wu C, Zeng X. Org. Lett. 2014; 16: 2248
40 Feng Y, Wang Y, Landgraf B, Liu S, Chen G. Org. Lett. 2010; 12: 3414
41 Huang Z, Dong G. J. Am. Chem. Soc. 2013; 135: 17747
42 Zhang SY, Li Q, He G, Nack WA, Chen G. J. Am. Chem. Soc. 2013; 135: 12135
43 Zhu RY, He J, Wang XC, Yu JQ. J. Am. Chem. Soc. 2014; 136: 13194
44 Chan KS. L, Wasa M, Chu L, Laforteza BN, Miura M, Yu J.-Q. Nat. Chem. 2014; 146
45 He J, Li S, Deng Y, Fu H, Laforteza BN, Spangler JE, Homs A, Yu JQ. Science 2014; 343: 1216
46 Guo L, Ma X, Fang H, Jia X, Huang Z. Angew. Chem. Int. Ed. 2015; 54: 4023
47 Yang W, Ye S, Fanning D, Coon T, Schmidt Y, Krenitsky P, Stamos D, Yu JQ. Angew. Chem. Int. Ed. 2015; 54: 2501