W. Bao, H. Kossen, U. Schneider
Mar 20, 2017
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Influential Citations
45
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Journal
Journal of the American Chemical Society
Abstract
The catalytic use of a sodium amide has been exploited for formal allylic C(sp3)-H bond activation of alkenes under mild conditions. Subsequent C-C bond formations with imines have proceeded in high yields with complete regioselectivity and excellent geometric selectivity. Aromatic cyano, chloro, and bromo functionalities are tolerated by the transition metal-free catalyst. Complex amines bearing a C═C double bond and distinct heteroaromatic units have been prepared in a single step. The critical importance of sodium versus other s-, p-, d-, and f-block metals as well as metal-free systems has been revealed. In addition, two catalytically active sodium-based intermediates were detected by NMR and HRMS analyses.