Cyclopentene Annulations of Alkene Radical Cations with Vinyl Diazo Species Using Photocatalysis | Zendy

Sarabia Francisco J. | Zendy; Li Qiankun | Zendy; Ferreira Eric M. | Zendy

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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.

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