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 Aug. 2018
Accepted
28 Sept. 2018
First published
03 Okt. 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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements