Efficient and Convenient Synthesis of β-Vinyl Sulfides in Nickel-Catalyzed Regioselective Addition of Thiols to Terminal Alkynes under Solvent-Free Conditions

Efficient and Convenient Synthesis of β-Vinyl Sulfides in Nickel-Catalyzed Regioselective Addition of Thiols to Terminal Alkynes under Solvent-Free Conditions Full article

Journal

Organometallics
ISSN: 1520-6041 , E-ISSN: 0276-7333

Output data

Year: 2006, Volume: 25, Number: 8, Pages: 1970-1977 Pages count : 8 DOI: 10.1021/om051105j

Authors

Ananikov Valentine P. ¹ , Orlov Nikolay V. ¹ , Beletskaya Irina P. ²

Affiliations

1	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow, 119991, Russia, and Chemistry Department, Lomonosov Moscow State University, Vorob'evy gory, Moscow, 119899, Russia
2	Chemistry Department, Lomonosov Moscow State University, Vorob'evy gory, Moscow, 119899, Russia

A new nanosized catalytic system has been developed for convenient preparation of β-vinyl sulfides H2CC(SAr)R with high yields (79−98%) and excellent selectivity (>98:2). Inexpensive and easily available Ni(acac)2 was used as catalyst precursor. Solvent-free conditions were combined with high atom efficiency of the ArSH addition reaction to terminal alkynes (HC⋮C−R) in order to create an environmentally friendly synthetic procedure. The mechanistic study has indicated that catalytic reaction takes place under heterogeneous conditions with alkyne insertion into the Ni−S bond as a key step.

Ananikov V.P. , Orlov N.V. , Beletskaya I.P.
Efficient and Convenient Synthesis of β-Vinyl Sulfides in Nickel-Catalyzed Regioselective Addition of Thiols to Terminal Alkynes under Solvent-Free Conditions
Organometallics. 2006. V.25. N8. P.1970-1977. DOI: 10.1021/om051105j WOS Scopus OpenAlex

Web of science:	WOS:000236700400019
Scopus:	2-s2.0-33646373908
OpenAlex:	W2110170720

DB	Citing
OpenAlex	113
Scopus	109
Web of science	106