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DOI: 10.1055/s-0036-1589008
Recent Progress in the Cross-Coupling Reaction Using Triorganosilyl-Type Reagents
Publication History
Received: 25 February 2017
Accepted after revision: 27 March 2017
Publication Date:
04 May 2017 (online)
Abstract
The silicon-based cross-coupling reaction has attracted much attention over recent decades because there are many advantages in using organosilicon compounds. However, the use of reagents with a triorganosilyl group as a key function remains to be established. This account summarizes our recent progress in cross-coupling chemistry with such silyl reagents.
1 Introduction
2 Preparation of HOMSi Reagents from Aryl Bromides and Disilanes
3 HOMSi Reagents from Heteroaromatics and Hydrosilanes
4 Cross-Coupling Polymerization with HOMSi Reagents
5 Cross-Coupling with Aryl(triethyl)silanes
6 Amination of Aryl Halides with N-TMS-Amines
7 Conclusion and Perspective
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References
- 1a Diederich F. Stang PJ. In Metal-Catalyzed Cross-Coupling Reactions . Wiley-VCH; Weinheim: 1998
- 1b de Meijere A. Diederich F. In Metal-Catalyzed Cross-Coupling Reactions . Wiley-VCH; Weinheim: 2004. 2nd ed.
- 2a Nakao Y. Hiyama T. Chem. Soc. Rev. 2011; 40: 4893
- 2b Sore HF. Galloway WR. J. D. Spring DR. Chem. Soc. Rev. 2012; 41: 1845
- 2c Denmark SE. Ambrosi A. Org. Process Res. Dev. 2015; 19: 982
- 2d Foubelo F. Najera C. Yus M. Chem. Rec. 2016; 16: 2521
- 2e Komiyama T. Minami Y. Hiyama T. ACS Catal. 2017; 7: 631
- 3 Hatanaka Y. Hiyama T. J. Org. Chem. 1988; 53: 918
- 4a Denmark SE. Choi Y. J. Am. Chem. Soc. 1999; 121: 5821
- 4b Denmark SE. Wehrli D. Choi Y. Org. Lett. 2000; 2: 2491
- 5a Itami K. Nokami T. Ishimura Y. Mitsudo K. Kamei T. Yoshida J. J. Am. Chem. Soc. 2001; 123: 11577
- 5b Itami K. Kamei T. Yoshida J. J. Am. Chem. Soc. 2003; 125: 14670
- 6 Hosoi K. Nozaki K. Hiyama T. Chem. Lett. 2002; 31: 138
- 7 Trost BM. Machacek MR. Ball ZT. Org. Lett. 2003; 5: 1895
- 8 Hanamoto T. Kobayashi T. J. Org. Chem. 2003; 68: 6354
- 9 Anderson JC. Munday RH. J. Org. Chem. 2004; 69: 8971
- 10 Katayama H. Nagao M. Moriguchi R. Ozawa F. J. Organomet. Chem. 2003; 676: 49
- 11 Li L. Navasero N. Org. Lett. 2006; 8: 3733
- 12 Sore HF. Blackwell DT. MacDonald SJ. F. Spring DR. Org. Lett. 2010; 12: 2806
- 13 Shindo M. Matsumoto K. Shishido K. Synlett 2005; 176
- 14a Nakao Y. Imanaka H. Sahoo AK. Yada A. Hiyama T. J. Am. Chem. Soc. 2005; 127: 6952
- 14b Nakao Y. Sahoo AK. Yada A. Chen J. Hiyama T. Sci. Technol. Adv. Mater. 2006; 7: 536
- 14c Nakao Y. Imanaka H. Chen J. Yada A. Hiyama T. J. Organomet. Chem. 2007; 692: 585
- 14d Nakao Y. Ebata S. Chen J. Imanaka H. Hiyama T. Chem. Lett. 2007; 36: 606
- 14e Nakao Y. Chen J. Tanada M. Hiyama T. J. Am. Chem. Soc. 2007; 129: 11694
- 14f Chen J. Tanaka M. Sahoo AK. Takeda M. Yada A. Nakao Y. Hiyama T. Bull. Chem. Soc. Jpn. 2010; 83: 554
- 14g Nakao Y. Takeda M. Matsumoto T. Hiyama T. Angew. Chem. Int. Ed. 2010; 49: 4447
- 15a Nakao Y. Oda T. Sahoo AK. Hiyama T. J. Organomet. Chem. 2003; 687: 570
- 15b Sahoo AK. Nakao Y. Hiyama T. Chem. Lett. 2004; 33: 632
- 15c Hiyama T. Sahoo AK. Oda T. Nakao Y. Adv. Synth. Catal. 2004; 346: 1715
- 16 Nokami T. Tomida Y. Kamei T. Itami K. Yoshida J. Org. Lett. 2006; 8: 729
- 17a Tang S. Takeda M. Nakao Y. Hiyama T. Chem. Commun. 2011; 47: 307
- 17b Ohgi A. Semba K. Hiyama T. Nakao Y. Chem. Lett. 2016; 45: 973
- 18a Pierrat P. Gros P. Fort Y. Org. Lett. 2005; 7: 697
- 18b Napier S. Marcuccio SM. Tye H. Whittaker M. Tetrahedron Lett. 2008; 49: 6314
- 19 Matsuda S. Takahashi M. Monguchi D. Mori A. Synlett 2009; 1941
- 20 Akai S. Ikawa T. Takayanagi S. Morikawa Y. Mohri S. Tsubakiyama M. Egi M. Wada Y. Kita Y. Angew. Chem. Int. Ed. 2008; 47: 7673
- 21 Murata M. Ohara H. Oiwa R. Watanabe S. Matsuda Y. Synthesis 2006; 1771
- 22 Chernyak N. Dudnik AS. Huang C. Gevorgyan V. J. Am. Chem. Soc. 2010; 132: 8270
- 23 Murai M. Takami K. Takeshima H. Takai K. Org. Lett. 2015; 17: 1798
- 24 Son EC. Tsuji H. Saeki T. Tamao K. Bull. Chem. Soc. Jpn. 2006; 79: 492
- 25a Smith AB. III. Hoye AT. Martinez-Solorio D. Kim Q.-S. Tong R. J. Am. Chem. Soc. 2012; 134: 4533
- 25b Martinez-Solorio D. Hoye AT. Nguyen MH. Smith III AB. Org. Lett. 2013; 15: 2454
- 25c Nguyen MH. Smith III AB. Org. Lett. 2013; 15: 4258
- 25d Nguyen MH. Smith III AB. Org. Lett. 2013; 15: 4872
- 25e Nguyen MH. Smith III AB. Org. Lett. 2014; 16: 2070
- 25f Martinez-Solorio D. Melillo B. Sanchez L. Liang Y. Lam E. Houk KN. Smith III AB. J. Am. Chem. Soc. 2016; 138: 1836
- 26a Iranpoor N. Firouzabadi H. Azadi R. J. Organomet. Chem. 2010; 695: 887
- 26b Lesbani A. Kondo H. Sato J. Yamanoi Y. Nishihara H. Chem. Commun. 2010; 46: 7784
- 26c Lesbani A. Kondo H. Yabusaki Y. Nakai M. Yamanoi Y. Nishihara H. Chem. Eur. J. 2010; 16: 13519
- 26d Huang C. Chernyak N. Dudnik AS. Gevorgyan V. Adv. Synth. Catal. 2011; 353: 1285
- 26e Kurihara Y. Nishikawa M. Yamanoi Y. Nishihara H. Chem. Commun. 2012; 48: 11564
- 26f Inubushi H. Kondo H. Lesbani A. Miyachi M. Yamanoi Y. Nishihara H. Chem. Commun. 2013; 49: 134
- 27a Gooßen LJ. Ferwanah A.-RS. Synlett 2000; 1801
- 27b Shirakawa E. Kurahashi T. Yoshida H. Hiyama T. Chem. Commun. 2000; 1895
- 27c Denmark SE. Kallemeyn JM. Org. Lett. 2003; 5: 3483
- 27d Iwasawa T. Komano T. Tajima A. Tokunaga M. Obora Y. Fujihara T. Tsuji Y. Organometallics 2006; 25: 4665
- 27e Kashiwabara T. Tanaka M. Organometallics 2006; 25: 4648
- 27f McNeill E. Barder TE. Buchwald SL. Org. Lett. 2007; 9: 3785
- 27g Yamamoto Y. Matsubara H. Murakami K. Yorimitsu H. Osuka A. Chem. Asian J. 2015; 10: 219
- 28a Zarate C. Martin R. J. Am. Chem. Soc. 2014; 136: 2236
- 28b Guo L. Chatupheeraphat A. Rueping M. Angew. Chem. Int. Ed. 2016; 55: 11810
- 29 Iizuka M. Kondo Y. Eur. J. Org. Chem. 2008; 1161
- 30 Minami Y. Shimizu K. Tsuruoka C. Komiyama T. Hiyama T. Chem. Lett. 2014; 43: 201
- 31 Shimizu K. Minami Y. Nakao Y. Ohya K. Ikehira H. Hiyama T. Chem. Lett. 2013; 42: 45
- 32a Cheng C. Hartwig JF. Chem. Rev. 2015; 115: 8946
- 32b Bähr S. Oestreich M. Angew. Chem. Int. Ed. 2017; 56: 52
- 33a Tsukada N. Hartwig JF. J. Am. Chem. Soc. 2005; 127: 5022
- 33b Murata M. Fukuyama N. Wada J. Watanabe S. Masuda Y. Chem. Lett. 2007; 36: 910
- 33c Lu B. Falck JR. Angew. Chem. Int. Ed. 2008; 47: 7508
- 33d Ishiyama T. Saiki T. Kishida E. Sasaki I. Ito H. Miyaura N. Org. Biomol. Chem. 2013; 11: 8162
- 33e Klare HF. T. Oestreich M. Ito J.-i. Nishiyama H. Ohki Y. Tatsumi K. J. Am. Chem. Soc. 2011; 133: 3312
- 33f Cheng C. Hartwig JF. Science 2014; 343: 853
- 33g Cheng C. Hartwig JF. J. Am. Chem. Soc. 2015; 137: 592
- 33h Murai M. Takami K. Takeshima H. Takai K. Org. Lett. 2015; 17: 1798
- 33i Murai M. Takami K. Takai K. Chem. Eur. J. 2015; 21: 4566
- 33j Yin Q. Klare HF. T. Oestreich M. Angew. Chem. Int. Ed. 2016; 55: 3204
- 33k Lee K.-S. Katsoulis D. Choi J. ACS Catal. 2016; 6: 1493
- 33l Fang H. Guo L. Zhang Y. Yao W. Huang Z. Org. Lett. 2016; 18: 5624
- 34 Toutov AA. Liu W.-B. Betz KN. Fedorov A. Stoltz BM. Grubbs RH. Nature 2015; 518: 80
- 35 Ma Y. Wang B. Zhang L. Hou Z. J. Am. Chem. Soc. 2016; 138: 3663
- 36 Chen Q.-A. Klare HF. T. Oestreich M. J. Am. Chem. Soc. 2016; 138: 7868
- 37 Minami Y. Komiyama T. Hiyama T. Chem. Lett. 2015; 44: 1065
- 38a Sakamoto J. Rehahn M. Wegner G. Schlüter AD. Macromol. Rapid Commun. 2009; 30: 653
- 38b Robb MJ. Ku S.-Y. Hawker CJ. Adv. Mater. 2013; 25: 5686
- 38c Carsten B. He F. Son HJ. Xu T. Yu L. Chem. Rev. 2011; 111: 1493
- 38d Bryan ZJ. McNeil AJ. Macromolecules 2013; 46: 8395
- 38e Yokozawa T. Nanashima Y. Ohta Y. ACS Macro Lett. 2012; 1: 862
- 39a Sengupta S. Sadbukhan SK. J. Chem. Soc., Perkin Trans. 1 1999; 2235
- 39b Nishihara Y. Ando J.-i. Kato T. Mori A. Hiyama T. Macromolecules 2000; 33: 2779
- 39c Mori A. Kondo T. Kato T. Nishihara Y. Chem. Lett. 2001; 30: 286
- 39d Babudri F. Colangiuli D. Lorenzo PA. D. Farinola GM. Omarb OH. Naso F. Chem. Commun. 2003; 39: 130
- 39e Katayama H. Nagao M. Moriguchi R. Ozawa F. J. Organomet. Chem. 2003; 676: 49
- 40a Kim Y. Cook S. Choulis SA. Nelson J. Durrant JR. Bradley DD. C. Chem. Mater. 2004; 16: 4812
- 40b Kabra D. Lu LP. Song MH. Snaith HJ. Friend RH. Adv. Mater. 2010; 22: 3194
- 40c Gwinner MC. Kabra D. Roberts M. Brenner TJ. K. Wallikewitz BH. McNeill CR. Friend RH. Sirringhaus H. Adv. Mater. 2012; 24: 2728
- 41 Wang N. Chen Z. Wei W. Jiang Z. J. Am. Chem. Soc. 2013; 135: 17060
- 42 Komiyama T. Minami Y. Hiyama T. Angew. Chem. Int. Ed. 2016; 55: 15787
- 43a Knapp DM. Gillis EP. Burke MD. J. Am. Chem. Soc. 2009; 131: 6961
- 43b Dick GR. Knapp DM. Gillis EP. Burke MD. Org. Lett. 2010; 12: 2314
- 43c Dick GR. Woerly EM. Burke MD. Angew. Chem. Int. Ed. 2012; 51: 2667
- 44 Hatanaka Y. Goda K.-i. Okahara Y. Hiyama T. Tetrahedron 1994; 50: 8301
- 45a Yoshida Y. Tamao K. Kakui T. Kurita A. Murata M. Yamada K. Kumada K. Organometallics 1982; 1: 369
- 45b Corc V. Chamoreau L. Derat E. Goddard J.-P. Ollivier C. Fensterbank L. Angew. Chem. Int. Ed. 2015; 54: 11414
- 45c Jouffroy M. Primer DN. Molander GA. J. Am. Chem. Soc. 2016; 138: 475
- 45d Patel NR. Kelly CB. Jouffroy M. Molander GA. Org. Lett. 2016; 18: 764
- 45e Xu P. Wang F. Fan G. Xu X. Tang P. Angew. Chem. Int. Ed. 2017; 56: 1101
- 46 F.-Rodríguez MA. Shen Q. Hartwig JF. J. Am. Chem. Soc. 2006; 128: 2180
- 47a Milton EJ. Fuentes JA. Clarke ML. Org. Biomol. Chem. 2009; 7: 2645
- 47b Bhadra S. Dzik WI. Gooßen LJ. J. Am. Chem. Soc. 2012; 134: 9938
- 48a Barluenga J. Aznar F. Valadés C. Angew. Chem. Int. Ed. 2004; 43: 343
- 48b Smith CJ. Early TR. Holmes AB. Shute RE. Chem. Commun. 2004; 1976
- 48c Smith CJ. Tsang MW. S. Holmes AB. Danheiser RL. Tester JW. Org. Biomol. Chem. 2005; 3: 3767
- 49a Ley SV. Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400
- 49b Evano G. Blanchard N. Toumi M. Chem. Rev. 2008; 108: 3054
- 49c Hartwig JF. Acc. Chem. Res. 2008; 41: 1534
- 49d Surry DS. Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 6338
- 49e Monnier F. Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954
- 49f Surry DS. Buchwald SL. Chem. Sci. 2010; 1: 13
- 49g Sadig JE. R. Willis MC. Synthesis 2011; 1
- 49h Surry DS. Buchwald SL. Chem. Sci. 2011; 2: 27
- 49i Beletskaya IP. Cheprakov AV. Organometallics 2012; 31: 7753
- 49j Rauws TR. M. Maes BU. W. Chem. Soc. Rev. 2012; 41: 2463
- 49k Ruiz-Castillo P. Buchwald SL. Chem. Rev. 2016; 116: 12564
- 50a Shimizu K. Minami Y. Goto O. Ikehira H. Hiyama T. Chem. Lett. 2014; 43: 438
- 50b Minami Y. Komiyama T. Shimizu K. Hiyama T. Goto O. Ikehira H. Bull. Chem. Soc. Jpn. 2015; 88: 1437
- 51a Adhikari RM. Neckers DC. J. Org. Chem. 2009; 74: 3341
- 51b Jiang W. Duan L. Qiao J. Dong G. Zhang D. Wang L. Qiu Y. J. Mater. Chem. 2011; 21: 4918
- 51c Uoyama H. Goushi K. Shizu K. Nomura H. Adachi C. Nature 2012; 492: 234
- 51d Chen Q. Luo M. Hammaeshøj P. Zhou D. Han Y. Laursen BW. Yan C.-G. Han B.-H. J. Am. Chem. Soc. 2012; 134: 6084
- 51e Komino T. Tanaka H. Adachi C. Chem. Mater. 2014; 26: 3665
- 51f Ishimatsu R. Matsunami S. Kasahara T. Mizuno J. Edura T. Adachi C. Nakano K. Imato T. Angew. Chem. Int. Ed. 2014; 53: 6993
- 52 Hooper MW. Utsunomiya M. Hartwig JF. J. Org. Chem. 2003; 68: 2861
- 53a Kanbara T. Honma A. 1996; 1135
- 53b Goodson FE. Hauck SI. Hartwig JF. J. Am. Chem. Soc. 1999; 121: 7527
- 54a Chen S.-A. Chuang K.-R. Chao C.-I. Lee H.-T. Synth. Met. 1996; 82: 207
- 54b Tu G. Zhou Q. Chen Y. Wang L. Ma D. Jing X. Wang F. Appl. Phys. Lett. 2004; 85: 2172
- 54c Lee SK. Hwang D.-H. Jung B.-J. Cho NS. Lee J. Lee J.-D. Shim H.-K. Adv. Funct. Mater. 2005; 15: 1647
- 54d Liu J. Zhou Q. Cheng Y. Geng Y. Wang L. Ma D. Jing X. Wang F. Adv. Mater. 2005; 17: 2974
- 55 Minami Y. Komiyama T. Shimizu K. Uno S. Hiyama T. Goto O. Ikehira H. Synlett 2017;
For recent reviews, see:
For recent examples, see:
For recent examples, see:
For recent reviews, see:
For selected examples of intermolecular catalytic dehydrogenative silylation of arenes without any directing group, see:
For recent reviews on the cross-coupling polymerization, see:
For reactions via single-electron transfer from silicates, see:
For reviews, see:
For selected examples, see:
For pioneering work on the Pd-catalyzed C–N cross-coupling polymerization, see: