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Synlett 2013; 24(15): 1882-1886
DOI: 10.1055/s-0033-1339684
DOI: 10.1055/s-0033-1339684
synpacts
Development and Challenges in the Copper-Catalyzed Trifluoromethylation of Alkenes
Weitere Informationen
Publikationsverlauf
Received: 07. Juli 2013
Accepted after revision: 09. August 2013
Publikationsdatum:
22. August 2013 (online)
Abstract
The recent trifluoromethylation of unactivated alkenes and related compounds provides a new and straightforward method to mainly form Csp3–CF3 bonds. However, several mechanisms have been proposed for the system of copper catalysts and electrophilic trifluoromethylating reagents. This paper differentiated the radical mechanism from others experimentally and computationally by investigating the chemoselectivity in the rearrangement of unsymmetrical α,α-diaryl allylic alcohols. Moreover, it outlines some future directions in this field.
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For selected reviews, see:
For recent selected examples, see:
For allylic trifluoromethylation of unactivated alkenes using a nucleophilic or radical trifluoromethylating reagent, see:
Oxytrifluoromethylation:
Carbotrifluoromethylation:
Hydrotrifluoromethylation:
Aminotrifluoromethylation:
For selectivity of radical 1,2-aryl migration (neophyl rearrangement), see:
For a review on radical aryl migration:
For selectivity of semipinacol rearrangement, see:
For a few examples for preparation of β-trifluoromethyl ketones, see: