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Cyclopentene Annulations of Alkene Radical Cations with Vinyl Diazo Species Using Photocatalysis
Author(s) -
Sarabia Francisco J.,
Li Qiankun,
Ferreira Eric M.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201805732
Subject(s) - diazo , cycloaddition , cyclopropanation , alkene , cyclopentene , chemistry , nucleophile , photocatalysis , photochemistry , electrophile , organic chemistry , catalysis
A direct (3+2) cycloaddition between alkenes and vinyl diazo reagents using either Cr or Ru photocatalysis is described. The intermediacy of a radical cation species enables a nucleophilic interception by vinyl diazo compounds, a departure from their traditional electrophilic behavior. A variety of cyclopentenes are synthesized using this method, and experimental insights implicate a direct cycloaddition instead of a cyclopropanation/rearrangement process.