Pd-NHC Catalytic System for the Efficient Atom-Economic Synthesis of Vinyl Sulfides from Tertiary, Secondary, or Primary Thiols

Pd-NHC Catalytic System for the Efficient Atom-Economic Synthesis of Vinyl Sulfides from Tertiary, Secondary, or Primary Thiols Full article

Journal

ACS Catalysis
ISSN: 2155-5435

Output data

Year: 2015, Volume: 5, Number: 12, Pages: 7208-7213 Pages count : 6 DOI: 10.1021/acscatal.5b01815

Authors

Degtyareva Evgeniya S. ¹ , Burykina Julia V. ¹ , Fakhrutdinov Artem N. ¹ , Gordeev Evgeniy G. ¹ , Khrustalev Victor N. ² , Ananikov Valentine P. ^1,3

Affiliations

1	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow, 119991, Russia
2	Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str., 28, Moscow, 119991, Russia
3	Department of Chemistry, Saint Petersburg State University, Stary Petergof, 198504, Russia

Vinyl sulfides represent an important class of compounds in organic chemistry and materials science. Atom-economic addition of thiols to the triple bond of alkynes provides an excellent opportunity for environmentally friendly processes. We have found that well-known and readily available Pd-NHC complex (IMes)Pd(acac)Cl is an efficient catalyst for alkyne hydrothiolation. The reported technique provides a general one-pot approach for the selective preparation of Markovnikov-type vinyl sulfides starting from tertiary, secondary, or primary aliphatic thiols, as well as benzylic and aromatic thiols. In all the studied cases, the products were formed in excellent selectivity and good yields.

Degtyareva E.S. , Burykina J.V. , Fakhrutdinov A.N. , Gordeev E.G. , Khrustalev V.N. , Ananikov V.P.
Pd-NHC Catalytic System for the Efficient Atom-Economic Synthesis of Vinyl Sulfides from Tertiary, Secondary, or Primary Thiols
ACS Catalysis. 2015. V.5. N12. P.7208-7213. DOI: 10.1021/acscatal.5b01815 WOS Scopus OpenAlex

≡ Web of science:	WOS:000366153300019
≡ Scopus:	2-s2.0-84948766939
≡ OpenAlex:	W2237263833