Alkene Synthesis by Photo-Wolff-Kischner Reaction of Sulfur Ylides and N-Tosylhydrazones

Autor:	Wen-Jing Xiao, Jia-Rong Chen, Min Jiang, Dong-Mei Yan, Ming-Hang Bi, Pan-Pan Gao
Rok vydání:	2021
Předmět:	chemistry.chemical_classification Chemistry Organic Chemistry Photoredox catalysis chemistry.chemical_element Substrate (chemistry) General Chemistry Sulfur Combinatorial chemistry Catalysis chemistry.chemical_compound Alkene synthesis Ylide Functional group Stereoselectivity Carbanion
Zdroj:	Chemistry (Weinheim an der Bergstrasse, Germany). 27(57)
ISSN:	1521-3765
Popis:	A visible-light-driven and room temperature photo-Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones has been developed for the first time to provide modular access to alkene synthesis. The high functional group tolerance and broad substrate scope were demonstrated by more than 60 examples. Both E- and Z-olefinic stereochemistry in the products could be controlled with excellent stereoselectivity. A series of mechanistic studies support that the reaction should proceed through a radical-carbanion crossover pathway, specifically involving addition of photo-generated sulfur ylide radical cations to N-tosylhydrazones to form carbanions and subsequent Wolff-Kischner process.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9e2c1eaae876b13a00d373775ea9a0d0 https://pubmed.ncbi.nlm.nih.gov/34374474 Zobrazit plný text záznamu Plný text ve formátu PDF