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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201805732
Subject(s) - diazo , cycloaddition , cyclopentene , alkene , cyclopropanation , nucleophile , chemistry , electrophile , photocatalysis , photochemistry , organic chemistry , medicinal 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.