Redox-Neutral Assembly of Selenobenzothiazine 1-Oxides via Rh(III)-Catalyzed Cascade [4 + 2] Annulation/Selenylation

Organic Letters 2026

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Authors: Yi Yang, Qingwei Song, L Q He, Dan Qiu, Cuishi Yan, X H Chen, Mei Wang, Shengdong Wang, Zhongyi Zeng, Y Wei, Zhi Zhou
DOI: 10.1021/acs.orglett.6c02774
Cited by: 1
References: 38

Abstract

The Rh(III)-catalyzed redox-neutral [4 + 2] annulation/selenylation of sulfoximines with vinyl selenones was realized to deliver the selenobenzothiazine 1-oxides with good compatibility and regioselectivity. The use of vinyl selenones achieves the effect of "three birds with one stone", which acted as the acetylene surrogate, the selenium source, and the internal oxidant. Further asymmetric synthesis was achieved with good enantioselectivity using an achiral Rh(III)/chiral phosphoric acid hybrid catalytic system, and the mechanistic study probed the sequential [4 + 2] annulation followed by the site-selective selenylation with the in situ-formed diselenide.

Fields of Study & Subjects

Organoselenium and organotellurium chemistry Catalytic C–H Functionalization Methods Sulfur-Based Synthesis Techniques

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
29
Pages
9553–9558
Publication date
11 July 2026
Language
EN