Issue 7, 2023

Deaminative coupling of benzylamines and arylboronic acids

Abstract

A metal-free deaminative coupling of non-prefunctionalised benzylamines and arylboronic acids is reported. In this operationally simple reaction, a primary amine in benzylamine is converted into a good leaving group in situ using inexpensive and commercially available isoamyl nitrite as a nitrosating reagent. Lewis-acidic arylboronic acids are shown to replace mineral acids such as HCl or HBF4 that are conventionally used in the preparation of aryl diazonium salts. This unlocked the formation of the corresponding diarylmethanes by forging a new C–C bond in good yields.

Graphical abstract: Deaminative coupling of benzylamines and arylboronic acids

Supplementary files

Article information

Article type
Edge Article
Submitted
02 Nov 2022
Accepted
30 Dec 2022
First published
13 Jan 2023
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., 2023,14, 1709-1714

Deaminative coupling of benzylamines and arylboronic acids

G. Sirvinskaite, J. C. Reisenbauer and B. Morandi, Chem. Sci., 2023, 14, 1709 DOI: 10.1039/D2SC06055H

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