Issue 15, 2025

Observation of the solvent enantio-isotope effect in asymmetric ring-opening of cyclic diaryliodoniums with selenocyanate

Abstract

A Cu-catalyzed asymmetric coupling reaction between cyclic diaryliodoniums and the ambident nucleophile KSeCN was reported. Utilizing water as a co-solvent (CH2Cl2/H2O) achieves high chemoselectivity by forming a nitrogen-hydrogen-bond, thereby blocking the N-site of ambident NCSe species, thus realizing efficient C–Se coupling. In contrast to the well-known kinetic isotope effect used to evaluate whether the C–H/D bond cleavage is rate-determining, the influence of deuterium-containing solvents on enantioselectivity remained largely unexplored. In this reaction, we observed a notable enhancement in enantioselectivity upon replacing H2O with D2O.

Graphical abstract: Observation of the solvent enantio-isotope effect in asymmetric ring-opening of cyclic diaryliodoniums with selenocyanate

Supplementary files

Article information

Article type
Edge Article
Submitted
02 Jan 2025
Accepted
11 Mar 2025
First published
11 Mar 2025
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., 2025,16, 6488-6494

Observation of the solvent enantio-isotope effect in asymmetric ring-opening of cyclic diaryliodoniums with selenocyanate

Y. Li, C. Tao, L. Duan and Z. Gu, Chem. Sci., 2025, 16, 6488 DOI: 10.1039/D5SC00014A

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