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Carbon‐Centered Radical Addition to C=X Bonds for C−X Bond Formation
Author(s) -
Liu Dong,
Liu Chao,
Lei Aiwen
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201500326
Subject(s) - radical , chemistry , heteroatom , photochemistry , carbon fibers , addition reaction , crystallography , organic chemistry , materials science , ring (chemistry) , catalysis , composite number , composite material
Among various kinds of radical reactions, the addition of carbon‐centered radicals to unsaturated bonds represents a powerful tool for the construction of different C−C and C−X (X=N, O, S, etc.) bonds, in which typically applied unsaturated bonds include alkenes, alkynes, imines, carbonyls, and even thiocarbonyls. When C=X bonds are utilized as the radical acceptors, reactions usually occur at the carbon position to generate a heteroatom radical, during which C−C coupling products are formed. This reaction mode has dominated this field for several decades. However, there is also another unconventional type of radical addition mode, in which carbon‐centered radicals attack the heteroatom position of C=X bonds to generate carbon radicals, during which selective C−X bond formation is achieved. This reaction mode demonstrates an effective method for the construction of different C−X bonds, such as C−O, C−N, and C−S bonds. This Focus Review gives an overview of recent advances in this unconventional field.