Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 34, Pages 11015-11019Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201805732
Keywords
chromium; cycloaddition; diazo compounds; photocatalysis; ruthenium
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Funding
- NSF
- EPA through the Catalysis Collaboratory for Light-Activated Earth Abundant Reagents (C-CLEAR) [CHE-1339674]
- NSF Graduate Research Fellowship Program [03855002]
- NIH [S10RR028859]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1339674] Funding Source: National Science Foundation
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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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