Issue 14, 2021

Nickel-catalyzed Suzuki–Miyaura cross-coupling of C–F bonds

Abstract

The efficient Suzuki–Miyaura cross-coupling of ortho-fluoro aromatic secondary amides with aryl boronates is described. The use of KOtBu is essential for the reaction to proceed. The function of the base is to abstract a proton from an amide nitrogen to generate a weak conjugate base, such as an amidate, which functions as a directing group. The reaction proceeds effectively, even at 60 °C. The reaction exhibits a good tolerance for functional groups and a broad scope for aromatic amides.

Graphical abstract: Nickel-catalyzed Suzuki–Miyaura cross-coupling of C–F bonds

Supplementary files

Article information

Article type
Research Article
Submitted
27 Apr 2021
Accepted
14 May 2021
First published
14 May 2021

Org. Chem. Front., 2021,8, 3783-3787

Nickel-catalyzed Suzuki–Miyaura cross-coupling of C–F bonds

T. Zhang, I. Nohira and N. Chatani, Org. Chem. Front., 2021, 8, 3783 DOI: 10.1039/D1QO00656H

To request permission to reproduce material from this article, 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 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