SCHEDULED MAINTENANCE
Ir(iii)-catalyzed ortho C–H alkylations of (hetero)aromatic aldehydes using alkyl boron reagents†
Xiao-Yang
Chen 
*a
and
Erik J.
Sorensen
*a
*a
and
Erik J.
Sorensen
*a
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.
- This article is part of the themed collections: Most popular 2018-2019 catalysis articles and 2018 Chemical Science HOT Article Collection
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