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- Title
An Alkene-Promoted Borane-Catalyzed Highly Stereoselective Hydrogenation of Alkynes to Give Z- and E-Alkenes.
- Authors
Liu, Yongbing; Hu, Lianrui; Chen, Hui; Du, Haifeng
- Abstract
The stereoselective hydrogenation of alkynes to alkenes is an extremely useful transformation in synthetic chemistry. Despite numerous reports for the synthesis of Z-alkenes, the hydrogenation of alkynes to give E-alkenes is still not well resolved. In particular, selective preparation of both Z- and E-alkenes by the same catalytic hydrogenation system using molecular H2 has rarely been reported. In this paper, a novel strategy of using simple alkenes as promoters for the HB(C6F5)2-catalyzed metal-free hydrogenation of alkynes was adopted. Significantly, both Z- and E-alkenes can be furnished by hydrogenation with molecular H2 in high yields with excellent stereoselectivities. Further experimental and theoretical mechanistic studies suggest that interactions between H and F atoms of the alkene promoter, borane intermediate, and H2 play an essential role in promoting the hydrogenolysis reaction.
- Subjects
STEREOSELECTIVE reactions; HYDROGENATION; ALKENES; BORANES; ALKYNES
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 8, p3495
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201405388