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Trifluoromethylation‐Initiated Remote Cross‐Coupling of Carbonyl Compounds to Form Carbon–Heteroatom/Carbon Bonds
Author(s) -
Huang Lin,
Zheng ShengCai,
Tan Bin,
Liu XinYuan
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500629
Subject(s) - trifluoromethylation , nucleophile , chemistry , heteroatom , combinatorial chemistry , substrate (aquarium) , reactivity (psychology) , coupling reaction , reagent , trifluoromethyl , carbon fibers , photochemistry , computational chemistry , organic chemistry , catalysis , ring (chemistry) , materials science , medicine , alkyl , composite number , composite material , geology , oceanography , alternative medicine , pathology
Abstract By involving the reversal of conventional reactivity expectations without external oxidants, we describe a novel and convenient protocol of remote cross‐coupling of carbonyl compounds with a series of common and simple nucleophiles. This cross‐coupling is triggered by radical trifluoromethylation of alkenes, thereby achieving highly selective remote difunctionalization of alkenes and α‐position of the carbonyl group for facile access to trifluoromethyl α‐halo‐ and α‐cyanocarbonyl compounds. The reaction exhibits a broad substrate scope with excellent functionality tolerance and many different types of nucleophiles; further synthetic applicability of the obtained compounds proved to be suitable, thus showing great potential for synthetic utility.