Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 1, Pages 159-162Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b12997
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Funding
- German science foundation (DFG) [PA 1562/6-1]
- Fonds der Chemischen Industrie (FCI) [PA 1562/6-1]
- German science foundation (DFG) Gottfried Wilhelm Leibniz prize
- Fonds der Chemischen Industrie (FCI) Gottfried Wilhelm Leibniz prize
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A method for the metal-free reduction of carboxylic amides using oxalyl chloride as an activating agent and hydrogen as the final reductant is introduced. The reaction proceeds via the hydrogen splitting by B(2,60F(2)-C6H3)(3) in combination with chloride as the Lewis base. Density functional theory calculations support the unprecedented role of halides as active Lewis base components in the frustrated Lewis pair mediated hydrogen activation. The reaction displays broad substrate scope for tertiary benzoic acid amides and a-branched carboxamides.
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