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Carbon‐Centered Radical Addition to OC of Amides or Esters as a Route to CO Bond Formations
Author(s) -
Liu Dong,
Tang Shan,
Yi Hong,
Liu Chao,
Qi Xiaotian,
Lan Yu,
Lei Aiwen
Publication year - 2014
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.201404607
Subject(s) - radical , chemistry , amide , electron paramagnetic resonance , oxygen , carbon fibers , photochemistry , functional group , radical cyclization , organic chemistry , materials science , physics , nuclear magnetic resonance , composite number , composite material , polymer
Among various types of radical reactions, the addition of carbon radicals to unsaturated bonds is a powerful tool for constructing new chemical bonds, in which the typical applied unsaturated substrates include alkenes, alkynes and imines. Carbonyl is perhaps the most common unsaturated group in nature. This work demonstrates a novel CO bond formation through carbon‐centered radical addition to the carbonyl oxygen of amide or ester, in which amide and ester groups are easily activated through the radical process. EPR spectroscopy and radical clock experiments support the radical process for this transformation, and density functional theory (DFT) calculations support the possibility of carbon‐centered radical addition to the carbonyl oxygen of amides or esters.