Photoredox-Catalyzed Cyclobutane Synthesis by a Deboronative Radical Addition–Polar Cyclization Cascade

Chao Shu, Adam Noble, Varinder Kumar Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

35 Citations (Scopus)
277 Downloads (Pure)

Abstract

Photoredox-catalyzed methylcyclobutanations of alkylboronic esters are described. The reactions proceed through single-electron transfer induced deboronative radical addition to an electron-deficient alkene followed by single-electron reduction and polar 4-exo-tet cyclization with a pendant alkyl halide. Key to the success of the methodology was the use of easily oxidizable arylboronate complexes. Structurally diverse cyclobutanes are shown to be conveniently prepared from readily available alkylboronic esters and a range of haloalkyl alkenes. The mild reactions display excellent functional group tolerance, and the radical addition-polar cyclization cascade also enables the synthesis of 3-, 5-, 6-, and 7-membered rings.

Original languageEnglish
Pages (from-to)3870-3874
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number12
Early online date15 Feb 2019
DOIs
Publication statusPublished - 18 Mar 2019

Keywords

  • photoredox catalysis
  • cyclobutanes
  • boronic esters
  • radical-polar crossover
  • cascade

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