A stepwise one-pot synthesis of aliphatic thiols and their derivatives from acrylamides and sulfur

Elemental sulfur enables the convenient formation of CS bonds and the direct incoporation of SS bonds. The reactivity of easily accessible electron deficient alkenes towards sulfur, however, is barely disclosed. Herein, we investigated the reactivity of acrylamides with sulfur and eventually develop...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-06, Vol.2 (21), p.4361-4368
Main Authors: Németh, András Gy, Szabó, Renta, Németh, Krisztina, Keser, Gyrgy M, brányi-Balogh, Pter
Format: Article
Language:English
Subjects:
Alkenes
Sulfur
Thioethers
Thiols
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Summary:Elemental sulfur enables the convenient formation of CS bonds and the direct incoporation of SS bonds. The reactivity of easily accessible electron deficient alkenes towards sulfur, however, is barely disclosed. Herein, we investigated the reactivity of acrylamides with sulfur and eventually developed a new pseudo-multicomponent reaction for the preparation of polysulfides. Sequential one-pot reduction led to diversely substituted thiols. Additional third stage one-pot modifications provided thioethers, unsymmetric disulfide and thioester. Investigation of the reactivity of sulfur towards electron deficient alkenes revealed a new method to generate polysulfides from acrylamides, which can be further transformed to thiols and its derivatives.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00512c