Nucleophilic Trifluoromethylation Reactions of Organic Compounds with (Trifluoromethyl)trimethylsilane
2000; Elsevier BV; Volume: 56; Issue: 39 Linguagem: Inglês
10.1016/s0040-4020(00)00550-0
ISSN1464-5416
AutoresRajendra Prasad Singh, Jean’ne M. Shreeve,
Tópico(s)Cyclopropane Reaction Mechanisms
ResumoA one‐pot synthesis of fluorinated chiral alcohols from α‐bromoarylketones and fluoroalcohols is described. The fluorinated ketone intermediates were formed from α‐bromoarylketones with fluoroalcohols as nucleophiles and solvents, which were reduced subsequentially by adding a chiral Ru catalyst and a mixture of formic acid and triethyl amines (FA: TEA=1.1:1) as hydrogen donor to give 27 examples of fluorinated chiral alcohols in 60–93% yields and 85–98% ee values. Notably, K3PO4 acts as a base in nucleophilic substitution and an additive in reductive step to enhance the reactivity and enantioselectivity, which is crucial for constructing compatible conditions for one‐pot process. This one‐pot process is also applicable to gram‐scale synthesis.
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