Palladium-Catalyzed Highly Chemo- and Stereoselective Bisthiolation of Terminal Alkynes with Allyl Phenyl Sulfides via C-S Bond Cleavage.
J Org Chem
; 87(12): 7895-7904, 2022 06 17.
Article
em En
| MEDLINE
| ID: mdl-35666286
ABSTRACT
A facile and general method for palladium-catalyzed stereoselective bisthiolation of terminal alkynes with allyl phenyl sulfides has been developed. The scope and versatility of the reaction have been demonstrated, and a broad range of substrates bearing electron-donating and -withdrawing groups on the aromatic rings were all compatible with this reaction, providing the desired (Z)-1,2-dithio-1-alkenes in moderate to good yields. Preliminary mechanistic studies demonstrated that the sulfur source of the desired products may be successively incorporated into alkynes via C-S bond cleavage of two molecules of allyl phenyl sulfides and ruled out the possibility of vinyl sulfides, alkynyl sulfides, and disulfide intermediates being involved in this reaction.
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Base de dados:
MEDLINE
Assunto principal:
Paládio
/
Alcinos
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2022
Tipo de documento:
Article