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Electrophilic Vinylation of Thiols under Mild and Transition Metal‐Free Conditions
Author(s) -
Castoldi Laura,
Di Tommaso Ester Maria,
Reitti Marcus,
Gräfen Barbara,
Olofsson Berit
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202002936
Subject(s) - chemistry , regioselectivity , reagent , stereoselectivity , electrophile , reactivity (psychology) , transition metal , substrate (aquarium) , organic chemistry , combinatorial chemistry , electrophilic addition , catalysis , medicine , oceanography , alternative medicine , pathology , geology
The iodine(III) reagents vinylbenziodoxolones (VBX) were employed to vinylate a series of aliphatic and aromatic thiols, providing E ‐alkenyl sulfides with complete chemo‐ and regioselectivity, as well as excellent stereoselectivity. The methodology displays high functional group tolerance and proceeds under mild and transition metal‐free conditions without the need for excess substrate or reagents. Mercaptothiazoles could be vinylated under modified conditions, resulting in opposite stereoselectivity compared to previous reactions with vinyliodonium salts. Novel VBX reagents with substituted benziodoxolone cores were prepared, and improved reactivity was discovered with a dimethyl‐substituted core.