Selective C–Si Bond Formation through C–H Functionalization

Ritika Sharma; Rakesh Kumar; Inder Kumar; Bikram Singh; Upendra Sharma

doi:10.1055/s-0034-1380435

Synthesis, Table of Contents

Synthesis 2015; 47(16): 2347-2366
DOI: 10.1055/s-0034-1380435

short review

Selective C–Si Bond Formation through C–H Functionalization

Ritika Sharma

Natural Product Chemistry and Process Development Division, CSIR-Institute of Himalayan Bioresource Technology, Palampur, Himachal Pradesh 176 061, India Email: upendra@ihbt.res.in

,

Rakesh Kumar

Natural Product Chemistry and Process Development Division, CSIR-Institute of Himalayan Bioresource Technology, Palampur, Himachal Pradesh 176 061, India Email: upendra@ihbt.res.in

,

Inder Kumar

Natural Product Chemistry and Process Development Division, CSIR-Institute of Himalayan Bioresource Technology, Palampur, Himachal Pradesh 176 061, India Email: upendra@ihbt.res.in

,

Bikram Singh

Natural Product Chemistry and Process Development Division, CSIR-Institute of Himalayan Bioresource Technology, Palampur, Himachal Pradesh 176 061, India Email: upendra@ihbt.res.in

,

Upendra Sharma*

Natural Product Chemistry and Process Development Division, CSIR-Institute of Himalayan Bioresource Technology, Palampur, Himachal Pradesh 176 061, India Email: upendra@ihbt.res.in

› Author Affiliations

Abstract

All articles of this category

Abstract

Silylation of hydrocarbons is one of the most important transformations due to the diverse application of organosilanes. Continuous progress is being made in organosilane synthesis particularly through direct C–H activation/functionalization. This minireview compiles various processes reported for C–Si bond formation from 2000–2014, through C–H activation/functionalization (proximal and remote) and metal-free approaches.

1 Introduction

2 C–Si Bond Formation through C–H Activation in Intermolecular Fashion

2.1 C–Si Bond Formation through Direct C(sp²)–H Activation

2.2 C–Si Bond Formation through Directing Group Assisted C(sp²)–H Activation

2.3 C–Si Bond Formation through sp³ C–H Activation

3 C–Si Bond Formation through Proximal C–H Activation/Functionalization in Intramolecular Fashion

3.1 Intramolecular C–Si Bond Formation through C(sp²)–H Activation

3.2 Intramolecular C–Si Bond Formation through C(sp³)–H Activation

4 Siloles Synthesis through Heteroannulation

5 C–Si Bond Formation through Remote C–H Activation

6 C–Si Bond Formation through C–O Bond Cleavage

7 Metal-Free Methods for C–Si Bond Formation

8 Summary and Outlook

Key words

silylation - C–H activation - catalytic - metal-free - siloles

Full Text

References

References

1a Bains W, Tacke R. Curr. Opin. Drug Discovery Dev. 2003; 6: 526
1b Showell GA, Mills JS. Drug Discovery Today 2003; 551
1c Wang J, Ma C, Wu Y, Lamb RA, Pinto LH, DeGrado WF. J. Am. Chem. Soc. 2011; 133: 13844

2a Mark JE. Acc. Chem. Res. 2004; 37: 946
2b Kawahara K, Hagiwara Y, Kuroda K. Chem. Eur. J. 2011; 17: 13188
2c Jones RG, Ando W, Chojnowski J. Silicon-Containing Polymers: The Science and Technology of Their Synthesis and Applications. Kluwer Academic; Dordrecht: 2000

3a Panek M, Masse CE. Chem. Rev. 1995; 95: 1293
3b Langkopf E, Schinzer D. Chem. Rev. 1995; 95: 1375
3c Fleming I, Barbero A, Walter D. Chem. Rev. 1997; 97: 2063

4a Waterman R, Hayes PG, Tilley TD. Acc. Chem. Res. 2007; 40: 712
4b Blom B, Stoelzel M, Driess M. Chem. Eur. J. 2013; 19: 40
4c Gallego D, Brück A, Irran E, Meier F, Kaupp M, Driess M, Hartwig JF. J. Am. Chem. Soc. 2013; 135: 15617

5a Li L, Zhang Y, Gao L, Song Z. Tetrahedron Lett. 2015; 56: 1466
5b Denmark SE, Sweis RF. Organosilicon Compounds in Cross-Coupling Reactions . In Metal-Catalyzed Cross-Coupling Reactions . Vol. 1. de Meijere A, Diederich F. Chap. Wiley-VCH; Weinheim: 2004
5c Denmark SE, Regens CS. Acc. Chem. Res. 2008; 41: 1486
5d Braunstein P, Knorr M. J. Organomet. Chem. 1995; 500: 21

6a Connolly JW, Urry G. J. Org. Chem. 1964; 29: 619
6b Marciniec B. Comprehensive Handbook of Hydrosilylation . Pergamon; New York: 1992
6c Lewis KM, Rethwisch DG. Catalyzed Direct Reactions of Silicon . Elsevier; New York: 1993
6d Missaghi MN, Downing CM, Kung MC, Kung HH. Organometallics 2008; 27: 6364

7a Rochow EG. J. Am. Chem. Soc. 1945; 67: 963
7b Lewis KM, Rethwisch DG. Catalyzed Direct Reactions of Silicon . Elsevier; New York: 1993

8 Marciniec B. Comprehensive Handbook of Hydrosilylation . Pergamon; New York: 1992

9a Barry AJ. US 2,499,561, 1950
9b Barry AJ. US 2,626,269, 1953
9c Barry AJ, Gilkey JW, Hook DE. Metal-Organic Compounds . ACS Advances in Chemistry Series 23; Washington: 1959

10a Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
10b Sharma U, Modak A, Maity S, Maji A, Maiti D. Direct Arylation via C–H Activation . In Introduction to New Trends in Cross-Coupling: Theory and Applications . Colacot T. RSC; Cambridge: 2014. Chap. 12, 551
10c Wu Y, Wang J, Mao F, Kwong FY. Chem. Asian J. 2014; 9: 26

11 Sakakura T, Tokunaga Y, Sodeyama T, Tanaka M. Chem. Lett. 1987; 2375
12 Ezbiansky K, Djurovich PI, Laforest M, Sinning DJ, Zayes R, Berry DH. Organometallics 1998; 17: 1455
13 Ishiyama T, Sato K, Nishio Y, Miyaura N. Angew. Chem. Int. Ed. 2003; 42: 5346
14 Ishiyama T, Sato K, Nishio Y, Saiki T, Miyaura N. Chem. Commun. 2005; 5065
15 Saiki T, Nishio Y, Ishiyama T, Miyaura N. Organometallics 2006; 25: 6068
16 Tsukada N, Hartwig JF. J. Am. Chem. Soc. 2005; 127: 5022
17 Klare HF. T, Oestreich M, Ito J, Nishiyama H, Ohki Y, Tatsumi K. J. Am. Chem. Soc. 2011; 133: 3312
18 Murai M, Takami K, Takai K. Chem. Eur. J. 2015; 21: 4566
19 Sasaki M, Kondo Y. Org. Lett. 2015; 17: 848
20 Kakiuchi F, Matsumoto M, Sonoda M, Fukuyama T, Chatani N, Murai S, Furukawa N, Seki Y. Chem. Lett. 2000; 750
21 Kakiuchi F, Igi K, Matsumoto M, Chatani N, Murai S. Chem. Lett. 2001; 422
22 Kakiuchi F, Igi K, Matsumoto M, Hayamizu T, Chatani N, Murai S. Chem. Lett. 2002; 396
23 Kakiuchi F, Matsumoto M, Tsuchiya K, Igi K, Hayamizu T, Chatani N, Murai S. J. Organomet. Chem. 2003; 686: 134
24 Tobisu M, Ano Y, Chatani N. Chem. Asian J. 2008; 3: 1585
25 Ihara H, Suginome M. J. Am. Chem. Soc. 2009; 131: 7502
26 Simmons EM, Hartwig JF. J. Am. Chem. Soc. 2010; 132: 17092
27 Li Q, Driess M, Hartwig JF. Angew. Chem. Int. Ed. 2014; 53: 8471
28 Choi G, Tsurugi H, Mashima K. J. Am. Chem. Soc. 2013; 135: 13149
29 Kanyiva KS, Kuninobu Y, Kanai M. Org. Lett. 2014; 16: 1968
30 Xiao Q, Meng X, Kanai M, Kuninobu Y. Angew. Chem. Int. Ed. 2014; 53: 3168
31 Hua Y, Asgari P, Dakarapu US, Jeon J. Chem. Commun. 2015; 51: 3778
32 Kakiuchi F, Tsuchiya K, Matsumoto M, Mizushima E, Chatani N. J. Am. Chem. Soc. 2004; 126: 12792
33 Mita T, Michigami K, Sato Y. Org. Lett. 2012; 14: 3462
34 Mita T, Michigami K, Sato Y. Chem. Asian J. 2013; 8: 2970
35 Li B, Driess M, Hartwig JF. Nature (London) 2014; 483: 70
36 Li B, Driess M, Hartwig JF. J. Am. Chem. Soc. 2014; 136: 6586

37a Yamaguchi S, Tamao K. J. Organomet. Chem. 2002; 653: 223
37b Hissler M, Dyer PW, Réau R. Coord. Chem. Rev. 2003; 244: 1
37c Yamaguchi S, Xu C, Okamoto T. Pure Appl. Chem. 2006; 78: 721
37d Corey JY. Adv. Organomet. Chem. 2011; 59: 181

38 Corey JY. Synthesis of Siloles (and Germoles) that Exhibit the AIE Effect. In Aggregation-Induced Emission: Fundamentals. Qin A, Tang BZ. Wiley; Chichester: 2013. Chap. 1
39 Ureshino T, Takuya T, Kuninobu Y, Takai K. J. Am. Chem. Soc. 2010; 132: 14324
40 Kuninobu Y, Yamauchi K, Tamura N, Seiki T, Takai K. Angew. Chem. Int. Ed. 2013; 52: 1520
41 Kuznetsov A, Gevorgyan V. Org. Lett. 2012; 14: 914
42 Kuznetsov A, Onishi Y, Inamoto Y, Gevorgyan V. Org. Lett. 2013; 15: 2498
43 Kuninobu Y, Nakahara T, Takeshima H, Takai K. Org. Lett. 2013; 15: 426

44a Tobisu M, Onoe M, Kita Y, Chatani N. J. Am. Chem. Soc. 2009; 131: 7506
44b Onoe M, Baba K, Kim Y, Kita Y, Tobisu M, Chatani N. J. Am. Chem. Soc. 2012; 134: 19477

45 Liang Y, Zhang S, Xi Z. J. Am. Chem. Soc. 2011; 133: 9204
46 Liang Y, Geng W, Wei J, Xi Z. Angew. Chem. Int. Ed. 2012; 51: 1934
47 Cheng C, Hartwig JF. Science (Washington, D.C.) 2014; 343: 853
48 Cheng C, Hartwig JF. J. Am. Chem. Soc. 2014; 136: 12064
49 Cheng C, Hartwig JF. J. Am. Chem. Soc. 2015; 137: 592
50 Zarate C, Martin R. J. Am. Chem. Soc. 2014; 136: 2236
51 Furukawa S, Kobayashi J, Kawashima T. J. Am. Chem. Soc. 2009; 131: 14192
52 Furukawa S, Kobayashi J, Kawashima T. Dalton Trans. 2010; 39: 9329
53 Curless LD, Ingleson MJ. Organometallics 2014; 33: 7241
54 O’Brien JM, Hoveyda AH. J. Am. Chem. Soc. 2011; 133: 7712
55 Ito H, Horita Y, Yamamoto E. Chem. Commun. 2012; 48: 8006

56a Ohmura T, Suginome M. Bull. Chem. Soc. Jpn. 2009; 82: 29
56b Beletskaya I, Moberg C. Chem. Rev. 1999; 99: 3435

57 Wang L, Zhu H, Guo S, Cheng J, Yu J.-T. Chem. Commun. 2014; 50: 10864
58 Gandhamsetty N, Joung S, Park S.-W, Park S, Chang S. J. Am. Chem. Soc. 2014; 136: 16780
59 During the preparation of this review, an excellent review on the same topic appeared in the literature, see: Cheng C, Hartwig JF. Chem. Rev. 2015; DOI: 10.1021/cr5006414