Cp∗Rh(III)-catalyzed electrophilic amination of arylboronic acids with azo compounds for synthesis of arylhydrazides

Yan Fung Lau, Chun Ming Chan, Zhongyuan Zhou, Wing Yiu Yu

Research output: Journal article publicationJournal articleAcademic researchpeer-review

10 Citations (Scopus)

Abstract

A [Cp∗Rh(iii)]-catalyzed electrophilic amination of arylboronic acids with diethyl azodicarboxylate (DEAD) was developed, and arylhydrazides were produced in excellent yields and selectivity. The analogous amination with the arylazocarboxylates afforded the corresponding N,N-diarylhydrazides. The electrophilic amination of arylboronic acids with azocarboxylates proceeds readily under mild conditions with excellent functional group tolerance. Up to 99% yields were obtained. Preliminary mechanistic studies revealed that prior formation of an arylrhodium(iii) intermediate for the azo coupling reaction can be ruled out.
Original languageEnglish
Pages (from-to)6821-6825
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number28
DOIs
Publication statusPublished - 1 Jan 2016

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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