Ortho-Deuteration of Aromatic Aldehydes via a Transient Directing Group-Enabled Pd-Catalyzed Hydrogen Isotope Exchange

Junhua Kong, Zhi Jiang Jiang, Jiayuan Xu, Yan Li, Hong Cao, Yanan Ding, Bencan Tang, Jia Chen, Zhanghua Gao

Research output: Journal PublicationArticlepeer-review

4 Citations (Scopus)

Abstract

A practical and scalable ortho-selective deuteration of aromatic aldehydes was accomplished by Pd-catalyzed hydrogen isotope exchange with deuterium oxide as an inexpensive deuterium source. The use of tert-leucine as a transient directing group facilitates the exchange, affording a wide range of ortho-deuterated aromatic aldehydes with deuterium incorporation up to 97%. The control experiments suggest that the addition of silver trifluoroacetate resists the unexpected reduction of Pd(II), while the theoretical study indicates a rapid reversible concerted metalation-deprotonation process.

Original languageEnglish
Pages (from-to)13350-13359
Number of pages10
JournalJournal of Organic Chemistry
Volume86
Issue number19
DOIs
Publication statusPublished - 1 Oct 2021

ASJC Scopus subject areas

  • Organic Chemistry

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