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

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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

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Publication details

The article was received on 14 Aug 2018, accepted on 28 Sep 2018 and first published on 03 Oct 2018


Article type: Edge Article
DOI: 10.1039/C8SC03606C
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    Ir(III)-catalyzed ortho C–H alkylations of (hetero)aromatic aldehydes using alkyl boron reagents

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

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