Issue 48, 2018

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

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.

Graphical abstract: Ir(iii)-catalyzed ortho C–H alkylations of (hetero)aromatic aldehydes using alkyl boron reagents

Supplementary files

Article information

Article type
Edge Article
Submitted
14 8 2018
Accepted
28 9 2018
First published
03 10 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2018,9, 8951-8956

Ir(III)-catalyzed ortho C–H alkylations of (hetero)aromatic aldehydes using alkyl boron reagents

X. Chen and E. J. Sorensen, Chem. Sci., 2018, 9, 8951 DOI: 10.1039/C8SC03606C

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