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Copper‐Catalyzed Radical Cross‐Coupling of Oxime Esters and Sulfinates for Synthesis of Cyanoalkylated Sulfones
Author(s) -
Zhou XueSong,
Cheng Ying,
Chen Jun,
Yu XiaoYe,
Xiao WenJing,
Chen JiaRong
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201901695
Subject(s) - chemistry , oxime , nucleophile , catalysis , pharmacophore , copper , combinatorial chemistry , bond cleavage , organic chemistry , polymer chemistry , stereochemistry
Sulfones and alkylnitriles play a significant role in both organic and medicinal chemistry, as versatile synthetic building blocks and privileged pharmacophores in many natural products and bioactive compounds. Herein, a room‐temperature, copper‐catalyzed radical cross‐coupling of redox‐active cycloketone oxime esters and sulfinate salts is described for the first time. Key to the success of this process involves catalytic generation of a cyclic iminyl radical and ensuing ring‐opening C−C bond cleavage. The resultant cyanoalkyl radical is then engaged in cross‐coupling with nucleophilic sulfinate to form cyanoalkylated sulfones.

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