Hydroesterification and difunctionalization of olefins with N-hydroxyphthalimide esters

Lingying Leng, Joseph M. Ready

Research output: Contribution to journalArticlepeer-review

Abstract

Irradiation of aryl esters of N-hydroxyphthalimides in the presence of unactivated olefins promotes a mild and regioselective hydroesterification. Optimal results are obtained with the aid of fac-Ir(dFppy)3 in CH2Cl2. Terminal and 1,1-disubstituted olefins provide primary esters, and trisubstituted olefins provide secondary esters. The anti-Markovnikov selectivity is consistent with alkyl radical intermediates, which are also indicated by the formation of cyclized products from dienes. Monoacylated diols are formed from trisubstituted and tetrasubstituted olefins in the presence of water.

Original languageEnglish (US)
Pages (from-to)13714-13720
Number of pages7
JournalACS Catalysis
Volume11
Issue number21
DOIs
StatePublished - Nov 5 2021

Keywords

  • Aminohydroxylation
  • Anti-Markovnikov
  • Dihydroxylation
  • Hydroesterification
  • Photocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint

Dive into the research topics of 'Hydroesterification and difunctionalization of olefins with N-hydroxyphthalimide esters'. Together they form a unique fingerprint.

Cite this