Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2017; 49(17): 3962-3967
DOI: 10.1055/s-0036-1589039
DOI: 10.1055/s-0036-1589039
paper
A Neutral Metal-Free System for Head-to-Tail Dimerization of Electron-Rich Alkenes
We gratefully acknowledge the National Science Foundation of China (21602213, 21522208, and 21372209) for financial support.Further Information
Publication History
Received: 30 March 2017
Accepted after revision: 05 May 2017
Publication Date:
20 June 2017 (online)
Abstract
A neutral metal-free system for the head-to-tail dimerization of electron-rich alkenes with stoichiometric amount of BrCCl2H and NaI is reported. This reaction proceeds under mild conditions with high efficiency and broad scope.
Supporting Information
- Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589039.
- Supporting Information
-
References
- 1a Mona H.-S. Zahra R. Mohammad MD. Appl. Catal. A 2014; 475: 477
- 1b Huo C. Wang Y. Yuan Y. Chen F. Tang J. Chem. Commun. 2016; 52: 7233
- 1c Nagata Y. Nishikawa T. Suginome M. J. Am. Chem. Soc. 2014; 136: 15901
- 1d Singh AS. Shendage SS. Nagarkar JM. Tetrahedron Lett. 2013; 54: 6319
- 1e Fumagalli G. Rabet PT. G. Boyd S. Greaney MF. Angew. Chem. Int. Ed. 2015; 54: 11481
- 1f Rogers MM. Kotov V. Chatwichien J. Stahl SS. Org. Lett. 2007; 9: 4331
- 1g Xia X.-F. Zhu S.-L. Gu Z. Wang H. Li W. Liu X. Liang Y.-M. J. Org. Chem. 2015; 80: 5572
- 1h Liu PN. Xia F. Zhao ZL. Wang QW. Ren YJ. Tetrahedron Lett. 2011; 52: 6113
- 1i Wang S. He L.-Y. Guo L.-N. Synthesis 2015; 47: 3191
- 2a Klemm D. Schumann D. Udhardt U. Marsch S. Prog. Polym. Sci. 2001; 26: 1561
- 2b Domski GJ. Rose JM. Coates GW. Bolig AD. Brookhart M. Prog. Polym. Sci. 2007; 32: 30
- 2c Masuda T. Isobe E. Higashimura T. J. Am. Chem. Soc. 1983; 105: 7473
- 2d Sui X. Yuan J. Zhou M. Zhang J. Yang H. Yuan W. Wei Y. Pan C. Biomacromolecules 2008; 9: 2615
- 3a Kondo T. Takagi D. Tsujita H. Ura Y. Wada K. Mitsudo T. Angew. Chem. Int. Ed. 2007; 46: 5958
- 3b Hiroi Y. Komine N. Komiya S. Hirano M. Organometallics 2014; 33: 6604
- 3c Erver F. Kuttner JR. Hilt G. J. Org. Chem. 2012; 77: 8375
- 4a Yi C. Hua R. Zeng H. Catal. Commun. 2008; 9: 85
- 4b Tsuchimoto T. Kamiyama S. Negoro R. Shirakawa E. Kawakami Y. Chem. Commun. 2003; 852
- 4c Shimura S. Miura H. Tsukada S. Wada K. Hosokawa S. Inoue M. ChemCatChem 2012; 4: 2062
- 4d Wang C.-C. Lin P.-S. Cheng C.-H. Tetrahedron Lett. 2004; 45: 6203
- 5 Yue H.-L. Zhao X.-H. Jiang L. Shao Y. Mei L.-J. Synth. Commun. 2016; 46: 179
- 6 Wang D. Fang Y. Xie Q. Yan Z. Lin S. Guo S. Synlett 2016; 27: 2815
- 7 Ma H. Sun Q. Li W. Wang J. Zhang Z. Yang Y. Lei Z. Tetrahedron Lett. 2011; 52: 1569
- 8 Liu K. Wang Y. Li P. Cai W. Xiang J. Catal. Commun. 2012; 20: 107
- 9 Iqbal N. Blakstad G. Fiksdahl A. Tetrahedron 2014; 70: 1317