A General Protocol for Radical Anion [3+2] Cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis

Adrian G. Amador, Evan M. Sherbrook, Zhan Lu, Tehshik P. Yoon

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

A method for intermolecular [3+2] cycloaddition between aryl cyclopropyl ketones and alkenes involving the combination of Lewis acid and photoredox catalysis is reported. In contrast to other more common methods for [3+2] cycloaddition, these conditions operate using a broad range of both electron-rich and electron-deficient reaction partners. The critical factors predicting the success of these reactions is the redox potential of the cyclopropyl ketone and the ability of the alkene to stabilize a key radical intermediate.

Original languageEnglish (US)
Article numberss-2017-m0573-op
Pages (from-to)539-547
Number of pages9
JournalSynthesis (Germany)
Volume50
Issue number3
DOIs
StatePublished - Feb 1 2018

Bibliographical note

Funding Information:
This work was conducted using funding from the NIH (GM095666). The mass spectroscopy facilities at UW-Madison are funded in part

Keywords

  • cycloaddition
  • cyclopentane
  • cyclopropane
  • photocatalysis
  • photoredox

Fingerprint Dive into the research topics of 'A General Protocol for Radical Anion [3+2] Cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis'. Together they form a unique fingerprint.

Cite this