Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 34, Pages 10145-10149Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201604921
Keywords
green chemistry; halogenation; homogenous catalysis; nucleophilic substitution; organocatalysis
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Funding
- Deutsche Forschungsgemeinschaft
- Fonds of the Chemical Industry (Liebig fellowship)
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A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99% -> >= 95% ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.
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