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Cross‐Coupling Reaction of Dimer‐Derived Persistent Tertiary‐Carbon‐Centered Radicals with Azo Compounds
Author(s) -
Ohnishi Rikako,
Sugawara Masumi,
Akakabe Mai,
Ezawa Tetsuya,
Koshino Hiroyuki,
Sohtome Yoshihiro,
Sodeoka Mikiko
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900300
Subject(s) - chemistry , radical , dimer , coupling reaction , photochemistry , bond cleavage , cleavage (geology) , coupling (piping) , substrate (aquarium) , computational chemistry , organic chemistry , catalysis , oceanography , geotechnical engineering , fracture (geology) , engineering , geology , mechanical engineering
Cross‐coupling reactions using tertiary carbon‐centered radicals are an important class of transformations for constructing C( sp 3 )−C( sp 3 ) bonds, but the use of dimers as precursors of the persistent radicals is quite rare. Herein, we describe a radical‐based cross‐coupling reaction between dimers (prepared from 2‐oxindoles and benzofuranones) and azo compounds that proceeds simply upon heating the reaction mixture. We present a conformational analysis of the dimers and we characterize the generation of a persistent radical via cleavage of the elongated C(3)−C(3’) σ‐bond. The behavior of the dimers in solution was characterized by spectroscopic analysis, helping to provide a basis for expanding the substrate scope of the cross‐coupling reaction.