Subscribe to RSS
DOI: 10.1055/s-0037-1610266
Recent Progress in σ-Bond Cross-Exchange Reactions to Access Diverse Silacycles
We are grateful for the financial support from the National Natural Science Foundation of China (21602115), 1000-Talent Youth Program (020/BF180181), the Natural Science Foundation of Tianjin (18JCYBJC20400), the Fundamental Research Funds for the Central Universities and Nankai University.Publication History
Received: 15 June 2018
Accepted after revision: 10 August 2018
Publication Date:
30 August 2018 (online)
Abstract
The σ-bond cross-exchange reaction, which involves cleavage and subsequent exchange between different nonpolar σ-bonds, constitutes an attractive protocol for rapid access to organic skeletons with 100% atom economy. Herein, we give a brief summary of recent achievements in this approach for the synthesis of diverse silacycles, highlighting our recent advances in the first intermolecular σ-bond exchange between C–C bonds of cyclopropenones and C–Si bonds of (benzo)silacyclobutanes.
1 Introduction
2 σ-Bond Exchange-Reaction of Benzocyclobutanones to Silacycles
3 σ-Bond Exchange-Reaction of Ethyl Cyclopropylideneacetates to Silacycles
4 σ-Bond Exchange-Reaction of Cyclopropenones to Silacycles
5 Conclusion
-
References
- 1a Jun C.-H. Chem. Soc. Rev. 2004; 33: 610
- 1b Tobisu M. Chatani N. Chem. Soc. Rev. 2008; 37: 300
- 1c Bonesi SM. Fagnoni M. Chem. Eur. J. 2010; 16: 13572
- 1d Mack DJ. Njardarson JT. ACS Catal. 2013; 3: 272
- 1e Chen F. Wang T. Jiao N. Chem. Rev. 2014; 114: 8613
- 1f Liu H. Feng M. Jiang X. Chem. Asian J. 2014; 9: 3360
- 1g Souillart L. Cramer N. Chem. Rev. 2015; 115: 9410
- 1h Murakami M. Ishida N. J. Am. Chem. Soc. 2016; 138: 13759
- 1i Shaw MH. Bower JF. Chem. Commun. 2016; 10817
- 1j Chen P.-H. Billett BA. Tsukamoto T. Dong G. ACS Catal. 2017; 7: 1340
- 1k Fumagalli G. Stanton S. Bower JF. Chem. Rev. 2017; 117: 9404
- 1l Hirano K. Yorimitsu H. Oshima K. Chem. Commun. 2008; 3234
- 1m Zhang Q.-W. An K. He W. Synlett 2015; 26: 1145
- 1n Li L. Zhang Y. Gao L. Song Z. Tetrahedron Lett. 2015; 56: 1466
- 1o Komiyama T. Minami Y. Hiyama T. ACS Catal. 2017; 7: 631
- 2a Edelbach BL. Lachicotte RJ. Jones WD. Organometallics 1999; 18: 4660
- 2b Matsuda T. Kirikae H. Organometallics 2011; 30: 3923
- 2c Chatani N. Takeyasu T. Hanafusa T. Tetrahedron Lett. 1988; 29: 3979
- 2d Pohlmann T. de Meijere A. Org. Lett. 2000; 2: 3877
- 2e Suginome M. Matsuda T. Ito Y. J. Am. Chem. Soc. 2000; 122: 11015
- 2f Cheng Z.-L. Xiao J.-C. Liu C. Chen Q.-Y. Eur. J. Org. Chem. 2006; 5581
- 3a Bains W. Tacke R. Curr. Opin. Drug Discovery Dev. 2003; 6: 526
- 3b Showell GA. Mills JS. Drug Discovery Today 2003; 8: 551
- 3c Englebienne P. Hoonacker AV. Herst C. Drug Design Rev. 2005; 2: 467
- 3d Meanwell NA. J. Med. Chem. 2011; 54: 2529
- 3e Franz AK. Wilson SO. J. Med. Chem. 2013; 56: 388
- 3f Min GK. Hernández D. Skrydstrup T. Acc. Chem. Res. 2013; 46: 457
- 4a Hissler M. Dyer PW. Réau R. Coord. Chem. Rev. 2003; 244: 1
- 4b Yamaguchi S. Tamao K. Chem. Lett. 2005; 34: 2
- 4c Shimizu M. Hiyama T. Synlett 2012; 23: 973
- 4d He X. Baumgartner T. RSC Adv. 2013; 3: 11334
- 4e Parke SM. Boone MP. Rivard E. Chem. Commun. 2016; 9485
- 5a Franz AK. Woerpel KA. Acc. Chem. Res. 2000; 33: 813
- 5b Hirano K. Yorimitsu H. Oshima K. Chem. Commun. 2008; 3234
- 5c Bracegirdle S. Anderson EA. Chem. Soc. Rev. 2010; 39: 4114
- 5d Parasram M. Gevorgyan V. Acc. Chem. Res. 2017; 50: 2038
- 6 Ishida N. Ikemoto W. Murakami M. Org. Lett. 2012; 14: 3230
- 7 Ishida N. Ikemoto W. Murakami M. J. Am. Chem. Soc. 2014; 136: 5912
- 8 Okumura S. Sun F. Ishida N. Murakami M. J. Am. Chem. Soc. 2017; 139: 12414
- 9 Saito S. Yoshizawa T. Ishigami S. Yamasaki R. Tetrahedron Lett. 2010; 51: 6028
- 10a Kondo T. Kaneko Y. Taguchi Y. Nakamura A. Okada T. Shiotsuki M. Ura Y. Wada K. Mitsudo T. J. Am. Chem. Soc. 2002; 124: 6824
- 10b Wender PA. Paxton TJ. Williams TJ. J. Am. Chem. Soc. 2006; 128: 14814
- 10c Yu S. Li X. Org. Lett. 2014; 16: 1220
- 10d Xie F. Yu S. Qi Z. Li X. Angew. Chem. Int. Ed. 2016; 55: 15351
- 10e Kong L. Zhou X. Xu Y. Li X. Org. Lett. 2017; 19: 3644
- 11 Zhao W.-T. Gao F. Zhao D. Angew. Chem. Int. Ed. 2018; 57: 6329
- 12 Aborways MM. Moran WJ. J. Organomet. Chem. 2015; 797: 57