Quantum Dot-Catalyzed Photoreductive Removal of Sulfonyl-Based Protecting Groups

Kaitlyn A. Perez, Cameron R. Rogers, Emily A. Weiss

Research output: Contribution to journalArticlepeer-review

Abstract

This Communication describes the use of CuInS2/ZnS quantum dots (QDs) as photocatalysts for the reductive deprotection of aryl sulfonyl-protected phenols. For a series of aryl sulfonates with electron-withdrawing substituents, the rate of deprotection for the corresponding phenyl aryl sulfonates increases with decreasing electrochemical potential for the two electron transfers within the catalytic cycle. The rate of deprotection for a substrate that contains a carboxylic acid, a known QD-binding group, is accelerated by more than a factor of ten from that expected from the electrochemical potential for the transformation, a result that suggests that formation of metastable electron donor–acceptor complexes provides a significant kinetic advantage. This deprotection method does not perturb the common NHBoc or toluenesulfonyl protecting groups and, as demonstrated with an estrone substrate, does not perturb proximate ketones, which are generally vulnerable to many chemical reduction methods used for this class of reactions.

Original languageEnglish
Pages (from-to)14091-14095
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number33
DOIs
Publication statusPublished - Aug 10 2020

Keywords

  • copper indium sulfide
  • deprotection
  • phenylsulfonates
  • photocatalysis
  • quantum dots

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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