Journal
ORGANIC LETTERS
Volume 19, Issue 20, Pages 5565-5568Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02695
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Funding
- Dalhousie University
- NSERC Discovery Grant
- Nova Scotia Innovation and Research Scholarship
- Killam Foundation
- Nova Scotia Black and First Nations Entrance Scholarship
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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 alpha,beta 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.
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