Chiral ligands in hypervalent iodine compounds: synthesis and structures of binaphthyl-based λ3-iodanes

Zhang, Huaiyuan, Cormanich, Rodrigo A. and Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667 2022. Chiral ligands in hypervalent iodine compounds: synthesis and structures of binaphthyl-based λ3-iodanes. Chemistry - A European Journal 28 (5) , e202103623. 10.1002/chem.202103623

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Abstract

Several novel binaphthyl-based chiral hypervalent iodine(III) reagents have been prepared and structurally analyzed. Various asymmetric oxidative reactions were applied to evaluate the reactivities and stereoselectivities of those reagents. Moderate to excellent yields were observed, however, very low stereoselectivities were obtained. The NMR experiments indicate that these reagents are very easily hydrolyzed in either chloroform or DMSO solvents leading to limited stereoselectivities. It is concluded that the use of chiral ligands is an unsuccessful way to prepare efficient stereoselective iodine(III) reagents.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Wiley
ISSN:	0947-6539
Date of First Compliant Deposit:	18 November 2021
Date of Acceptance:	16 November 2021
Last Modified:	02 Dec 2024 14:00
URI:	https://orca.cardiff.ac.uk/id/eprint/145612

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