Ir(iii)-catalyzed: Ortho C-H alkylations of (hetero)aromatic aldehydes using alkyl boron reagents

Xiao Yang Chen, Erik J. Sorensen

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17 Scopus citations

Abstract

Transition-metal-catalyzed C-H alkylation reactions directed by aldehydes or ketones have been largely restricted to electronically activated alkenes. Herein, we report a general protocol for the Ir(iii)-catalyzed ortho C-H alkylations of (hetero)aromatic aldehydes using alkyl boron reagents as the coupling partner. Featuring aniline as an inexpensive catalytic ligand, the method was compatible with a wide variety of benzaldehydes, heterocyclic aldehydes, potassium alkyltrifluoroborates as well as a few α,β-unsaturated aldehydes. An X-ray crystal structure of a benzaldehyde ortho C-H iridation intermediate was also successfully obtained.

Original languageEnglish (US)
Pages (from-to)8951-8956
Number of pages6
JournalChemical Science
Volume9
Issue number48
DOIs
StatePublished - 2018

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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