Pd-Catalyzed debenzylation and deallylation of ethers and esters with sodium hydride

Yujian Mao, Ye Liu, Yanwei Hu, Liang Wang, Shilei Zhang, Wei Wang

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

Herein we demonstrate simply that the addition of Pd(OAc)2 as a promotor switches the reactivity of a commonly used base NaH to a nucleophilic reductant. The reactivity is engineered into a palladium-catalyzed reductive debenzylation and deallylation of aryl ethers and esters. This operationally simple, mild protocol displays a broad substrate scope and a broad spectrum of functional group tolerance (>50 examples) and high chemoselectivity toward aryl ethers over aliphatic structures. Moreover, the dual reactivity of NaH as a base and a reductant is demonstrated in efficient synthetic elaboration.

Original languageEnglish (US)
Pages (from-to)3016-3020
Number of pages5
JournalACS Catalysis
Volume8
Issue number4
DOIs
StatePublished - Apr 6 2018
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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