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Carbene‐Catalyzed Direct Functionalization of the β‐sp 3 ‐Carbon Atoms of α‐Chloroaldehydes
Author(s) -
Liu Bin,
Luo Guoyong,
Wang Hongling,
Hao Lin,
Yang Song,
Jin Zhichao,
Chi Yonggui Robin
Publication year - 2019
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.201903592
Subject(s) - carbene , catalysis , nucleophile , surface modification , chemistry , aldehyde , inert , carbon fibers , carbon atom , substrate (aquarium) , organic synthesis , photochemistry , combinatorial chemistry , organic chemistry , materials science , ring (chemistry) , composite material , geology , oceanography , composite number
A direct functionalization of the β‐sp 3 carbon atom of α‐chloro aldehyde has been developed. The reaction starts with the addition of a carbene catalyst to α‐chloroaldehyde to eventually form the homoenolate intermediate. This overall redox‐neutral process successfully converts the otherwise inert β‐sp 3 ‐carbon atom of the aldehyde substrate to a nucleophilic carbon atom for asymmetric reactions. This study constitutes the first success in activating α‐chloroaldehydes to generate homoenolate intermediates by carbene organic catalysis and shall encourage further explorations in using organic catalysis for transforming inert chemical bonds.