Journal
ORGANIC LETTERS
Volume 20, Issue 10, Pages 2980-2983Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01023
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Funding
- German Research Foundation (DFG)
- Fonds of the Chemical Industry (Liebig fellowship)
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A practical method for the nucleophilic substitution (S-N) of alcohols furnishing alkyl chlorides, bromides, and iodides under stereochemical inversion in high catalytic efficacy is introduced. The fusion of diethylcyclopropenone as a simple Lewis base organocatalyst and benzoyl chloride as a reagent allows notable turnover numbers up to 100. Moreover, the use of plain acetyl chloride as a stoichiometric promotor in an invertive S-N-type transformation is demonstrated for the first time. The operationally straightforward protocol exhibits high levels of stereoselectivity and scalability and tolerates a variety of functional
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