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Copper‐Catalyzed 1,6‐Hydrodifluoroacetylation of para ‐Quinone Methides at Ambient Temperature with Bis(pinacolato)diboron as Reductant
Author(s) -
Ke Miaolin,
Song Qiuling
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600991
Subject(s) - chemistry , catalysis , copper , quinone , organic chemistry , photochemistry
Abstract An original and efficient copper‐catalyzed 1,6‐hydrodifluoroacetylation of para ‐quinone methides with difluoroalkyl bromides has been described with bis(pinacolato)diboron (B 2 pin 2 ) as reductant. In this reaction, a new C( sp 3 )–CF 2 bond is constructed under smart conditions. A broad substrate scope of para ‐quinone methides ( p ‐QMs) make this protocol very practical and attractive. Preliminary mechanistic studies manifested that a difluoroalkyl radical pathway was involved in this reaction. Also the presence of the diboron reagent was an essential requisite in this transformation.