Organic Letters
Organic Letters
4 years ago

Hydroboration Catalyzed by 1,2,4,3-Triazaphospholenes

Hydroboration Catalyzed by 1,2,4,3-Triazaphospholenes
Chieh-Hung Tien, Michael J. Ferguson, Alexander W. H. Speed, Erin R. Johnson, Matt R. Adams
The synthesis and study of the catalytic activity of 1,2,4,3-triazaphospholenes (TAPs) is reported. TAPs represent a more modular scaffold than previously reported diazaphospholenes. TAP halides were shown to catalyze the 1,2 hydroboration of 19 imines, and three α,β unsaturated aldehydes with pinacolborane, including examples that did not undergo hydroboration by previously reported diazaphospholene systems. DFT calculations support a mechanism where a triazaphospholene cation interacts with the substrate, a mechanism distinct from diazaphospholene catalyzed hydroborations.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02695

DOI: 10.1021/acs.orglett.7b02695

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