Issue 22, 2021

Reactions promoted by hypervalent iodine reagents and boron Lewis acids

Abstract

Understanding the role of boranes in hypervalent iodine chemistry will open up new reactivities which can be utilised in organic synthesis. Due to similar reactivities, λ3-iodanes have presented themselves as viable alternatives for many transformations dominated by transition metals whilst mitigating some of the associated drawbacks of metal systems. As showcased by recent reports, boranes can adopt a dual role in hypervalent iodine chemistry that surpasses mere activation of the hypervalent iodine reagent. Increased efforts to harness this potential with diverse boranes will uncover exciting reactivity with high applicability across various disciplines including adoption in the pharmaceutical sciences. This review will be relevant to the wider synthetic community including organic, inorganic, materials, and medicinal chemists due to the versatility of hypervalent iodine chemistry especially in combination with borane activation or participation. We aim to highlight the development of hypervalent iodine compounds including their structure, bonding, synthesis and utility in metal-free organic synthesis in combination with Lewis acidic boranes.

Graphical abstract: Reactions promoted by hypervalent iodine reagents and boron Lewis acids

Article information

Article type
Review Article
Submitted
16 apr 2021
Accepted
13 may 2021
First published
13 may 2021
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2021,19, 4852-4865

Reactions promoted by hypervalent iodine reagents and boron Lewis acids

A. Dasgupta, C. Thiehoff, P. D. Newman, T. Wirth and R. L. Melen, Org. Biomol. Chem., 2021, 19, 4852 DOI: 10.1039/D1OB00740H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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