Visible-Light-Promoted Nickel- and Organic-Dye-Cocatalyzed Formylation Reaction of Aryl Halides and Triflates and Vinyl Bromides with Diethoxyacetic Acid as a Formyl Equivalent

He Huang, Xiangmin Li, Chenguang Yu, Yueteng Zhang, Patrick S. Mariano, Wei Wang

Research output: Contribution to journalArticlepeer-review

90 Scopus citations

Abstract

A simple formylation reaction of aryl halides, aryl triflates, and vinyl bromides under synergistic nickel- and organic-dye-mediated photoredox catalysis is reported. Distinct from widely used palladium-catalyzed formylation processes, this reaction proceeds by a two-step mechanistic sequence involving initial in situ generation of the diethoxymethyl radical from diethoxyacetic acid by a 4CzIPN-mediated photoredox reaction. The formyl-radical equivalent then undergoes nickel-catalyzed substitution reactions with aryl halides and triflates and vinyl bromides to form the corresponding aldehyde products. Significantly, besides aryl bromides, less reactive aryl chlorides and triflates and vinyl halides serve as effective substrates for this process. Since the mild conditions involved in this reaction tolerate a plethora of functional groups, the process can be applied to the efficient preparation of diverse aromatic aldehydes.

Original languageEnglish (US)
Pages (from-to)1500-1505
Number of pages6
JournalAngewandte Chemie - International Edition
Volume56
Issue number6
DOIs
StatePublished - Feb 2017
Externally publishedYes

Keywords

  • flow chemistry
  • formylation
  • nickel catalysis
  • photoredox catalysis
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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