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Remote C(sp 3 )−H Arylation and Vinylation of N ‐Alkoxypyridinium Salts to δ‐Aryl and δ‐Vinyl Alcohols
Author(s) -
Bao Xu,
Wang Qian,
Zhu Jieping
Publication year - 2019
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.201902918
Subject(s) - chemistry , aryl , radical , catalysis , medicinal chemistry , reductive elimination , nucleophile , hydrogen atom , alkyl , organic chemistry
The reaction of readily available and bench‐stable N ‐alkoxypyridinium salts with arylboronic and vinylboronic acids afforded δ‐aryl and δ‐vinyl alcohols, respectively, in the presence of fac ‐Ir(ppy) 3 and Cu(OTf) 2 dual catalysts. The reaction takes place through a domino process involving the reductive generation of alkoxyl radicals, 1,5‐hydrogen atom transfer (1,5‐HAT) and the copper‐catalyzed cross‐coupling reaction of the resulting translocated carbon radicals with boronic acids. Complementary to the Minisci reaction, this method allows for the arylation of nucleophilic alkyl radicals with both electron‐rich and electron‐poor arenes under mild reaction conditions.