Thiolation of Terminal Alkynes with Thiuram Disulfide Reagents Using Water as the Hydrogen Source: Stereoselective Synthesis of (Z)-Vinyl Sulfides.
J Org Chem
; 88(24): 16906-16914, 2023 Dec 15.
Article
in En
| MEDLINE
| ID: mdl-38019102
ABSTRACT
A stereoselective and environmentally friendly thiolation of terminal alkynes was reported. Thiuram disulfide reagents (tetramethylthiuram disulfide and tetraethylthiuram disulfide) that reacted with alkynes in dimethyl sulfoxide (DMSO)/H2O could give (Z)-vinyl sulfides in good yields (up to 88%). This protocol features broad substrate scope, good stereoselectivity, high atom economy, good yields, and is transition metal-free. Mechanistic studies revealed that water and DMSO served as hydrogen sources, which greatly highlighted the unique reactivity of this special reaction involving two H-atom donors.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
J Org Chem
Year:
2023
Type:
Article
Affiliation country:
China