Photocatalyzed Annulation‐Biselenylation of Enynone with Diarylselenides toward Biselenium‐Substituted 1‐Indanones under Metal‐ and Photosensitizer‐Free Conditions

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 17, 2025

Comprehensive Summary A practical photocatalytic annulation‐biselenylation strategy has been developed for the efficient synthesis of biselenium‐substituted 1‐indanones (38 examples in total) with generally good yields (up to 95%) and excellent stereoselectivity (>19 : 1 Z / E ratio) by employing enynones diaryl selenides as starting materials under photosensitizer‐free conditions. The reaction mechanism involves a cascade process comprising homolytic cleavage, radical addition, 5‐ exo ‐ dig cyclization, capture, enabling sequential formation multiple bonds, such C(sp 3 )‐Se, )‐C(sp 2 ), )‐Se rapidly construct molecular complexity. Notably, this approach demonstrates wide substrate compatibility tolerability towards various functional groups. It is further characterized its remarkable efficiency creating chemical bonds achieving high atomic utilization 100%.

Language: Английский

Amine-Promoted Three-Component Radical Selenofunctionalization for the Construction of β-Hydroxy Selenide Derivatives

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 28, 2024

An amine-promoted three-component radical selenofunctionalization reaction of alkenes with TBHP and diselenide is disclosed. The conditions are mild suitable for a wide range substrates (29 examples), all give the corresponding hydroxyselenenylation products in moderate to excellent yields. In addition, preliminary studies on mechanism reveal that current method might proceed via pathway. serves as both initiator source hydroxyl group.

Language: Английский