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Access to Difluoromethylated Alkynes through the Castro–Stephens Reaction
Author(s) -
Besset Tatiana,
Poisson Thomas,
Pannecoucke Xavier
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402937
Subject(s) - reagent , chemistry , combinatorial chemistry , reaction conditions , organic chemistry , catalysis
An efficient synthesis of difluoromethylated alkynes is described. A panel of readily available Cu I acetylides undergo direct difluoromethylation by using BrCF 2 CO 2 Et, which is an inexpensive, easy to handle, commercially available fluorinated reagent. The reaction, which is based on a Castro–Stephens transformation, proceeds smoothly under mild conditions offering a new synthetic route for the direct introduction of the difluoromethylated group into alkynes that does not involve ozone‐depleting reagents. The resulting products were obtained with good yields by using CsOPiv and Cu(OAc) 2 as additives.