Mechanophotocatalysis: a generalizable approach to solvent-minimized photocatalytic reactions for organic synthesis

Francis D. Millward, Eli Zysman-Colman*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

This proof-of-concept study cements the viability and generality of mechanophotocatalysis, merging mechanochemistry and photocatalysis to enable solvent-minimized photocatalytic reactions. We demonstrate the transmutation of four archetypal solution-state photocatalysis reactions to a solvent-minimized environment driven by the combined actions of milling, light, and photocatalysts. The chlorosulfonylation of alkenes and the pinacol coupling of aldehydes and ketones were conducted under solvent-free conditions with competitive or superior efficiencies to their solution-state analogues. Furthermore, decarboxylative alkylations are shown to function efficiently under solvent-minimized conditions, while the photoinduced energy transfer promoted [2+2] cycloaddition of chalcone experiences a significant initial rate enhancement over its solution-state variant. This work serves as a platform for future discoveries in an underexplored field: validating that solvent-minimized photocatalysis is not only generalizable and competitive with solution-state photocatalysis, but can also offer valuable advantages.
Original languageEnglish
Article numbere202316169
Number of pages10
JournalAngewandte Chemie International Edition
VolumeEarly View
Early online date19 Feb 2024
DOIs
Publication statusE-pub ahead of print - 19 Feb 2024

Keywords

  • Mechanochemistry
  • Photocatalysis
  • Synthetic methods
  • Mechanophotocatalysis
  • Radicals

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