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Catalytic migratory oxidative coupling of nitrones through an outer‐sphere C( sp 3 )‐H activation process
Author(s) -
Hashizume Shogo,
Oisaki Kounosuke,
Kanai Motomu
Publication year - 2011
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.201100024
Subject(s) - catalysis , oxidative coupling of methane , oxidative phosphorylation , coupling (piping) , process (computing) , chemistry , physics , photochemistry , crystallography , materials science , organic chemistry , biochemistry , computer science , metallurgy , operating system
Outer‐sphere redox catalysis is key to efficient C‐H activation, which has attracted increased interest in organic chemistry. In this account, we describe a Cu I ‐catalyzed oxidative coupling between nitrones and various ethers or amines as an example. Predictable site‐selective C‐C bond formation was achieved through activation of the C‐H bonds in each coupling partner and the migration of a C‐N double bond. Mechanistic studies strongly suggested that the reaction proceeded via an oxonium/iminium cation species as the key intermediate. The mechanistic information allows for future extension of outer‐sphere redox catalysis. DOI 10.1002/tcr.201100024