Synlett 2019; 30(08): 875-884
DOI: 10.1055/s-0037-1612109
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© Georg Thieme Verlag Stuttgart · New York

Diazonium Salts as Nitrogen-Based Lewis Acids

Evi R. M. Habraken
,
,
Van‘t Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1090 GD Amsterdam, The Netherlands   Email: j.c.slootweg@uva.nl
› Author Affiliations
This work was supported by the Council for Chemical Sciences of The Netherlands Organization for Scientific Research (NWO/CW) by a VIDI grant (J.C.S.) and a VENI grant (A.R.J.).
Further Information

Publication History

Received: 21 December 2018

Accepted after revision: 11 January 2019

Publication Date:
08 February 2019 (online)

Abstract

Aryldiazonium salts are widely used in many organic transformations with displacement of N2 or through addition to the terminal nitrogen. Such aryldiazonium salts can be viewed as N-based Lewis acids that can react with Lewis bases to synthesize a wide variety of azo compounds. Additionally, diazonium salts are known to undergo single-electron transfer and release N2, forming an aryl radical, which results in different reactivity. Herein, we provide a concise overview of the reactivity of aryldiazonium salts undergoing classical donor-acceptor reactivity or single-electron transfer.

 
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