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Reactions promoted by hypervalent iodine reagents and boron Lewis acids

Dasgupta, Ayan, Thiehoff, Christian, Newman, Paul D. ORCID: https://orcid.org/0000-0002-1808-1211, Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667 and Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831 2021. Reactions promoted by hypervalent iodine reagents and boron Lewis acids. Organic and Biomolecular Chemistry 19 (22) , pp. 4852-4865. 10.1039/D1OB00740H

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Additional Information: This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Publisher: Royal Society of Chemistry
ISSN: 1477-0520
Funders: EPSRC and Leverhulme Trust
Date of First Compliant Deposit: 24 May 2021
Date of Acceptance: 13 May 2021
Last Modified: 28 Nov 2022 12:51
URI: https://orca.cardiff.ac.uk/id/eprint/141532

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