期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 8, 页码 3495-3501出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201405388
关键词
alkene; alkyne; hydrogenation; metal-free catalysis; stereoselectivity
资金
- National Natural Science Foundation of China [21222207, 21290194, 21221002, 21473215]
- 973 program [2011CB808600]
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 H-2 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 H-2 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 H-2 play an essential role in promoting the hydrogenolysis reaction.
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