2018
DOI: 10.1002/ejoc.201801520
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Transition‐Metal‐Free C(sp3)–S Coupling in Water: Synthesis of Benzyl Dithiocarbamates Using Thiuram Disulfides as an Organosulfur Source

Abstract: A simple, highly efficient and environmentally benign method for the synthesis of benzyl dithiocarbamates was reported. Without addition of metal catalyst, a series of 34 benzyl dithiocarbamates were obtained in good to excellent yields by treating benzyl halides with tetraalkylthiuram disulfides in water. The protocol allows easy access to C(sp3)–S bond formation, features the advantages of easy performance, environmental friendliness, good to excellent yields, and good functional tolerance, showing potential… Show more

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Cited by 18 publications
(1 citation statement)
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“…As a result, development of efficient and novel methods for the synthesis of this kind of significant sulfur-containing compounds will be of great value for the screening of biologically active molecules. Traditionally, one-pot procedures by reaction of amines with carbon disulfide and alkyl halides have been demonstrated to be convenient methods for the synthesis of alkyl dithiocarbamates . However, approaches for the formation of aryl dithiocarbamates are quite limited and the available methods involved the Wittig reaction of aldehydes with phosphonium ylides and the reaction of the sodium salt of dithiocarbamic acid with hypervalent iodine compounds .…”
mentioning
confidence: 99%
“…As a result, development of efficient and novel methods for the synthesis of this kind of significant sulfur-containing compounds will be of great value for the screening of biologically active molecules. Traditionally, one-pot procedures by reaction of amines with carbon disulfide and alkyl halides have been demonstrated to be convenient methods for the synthesis of alkyl dithiocarbamates . However, approaches for the formation of aryl dithiocarbamates are quite limited and the available methods involved the Wittig reaction of aldehydes with phosphonium ylides and the reaction of the sodium salt of dithiocarbamic acid with hypervalent iodine compounds .…”
mentioning
confidence: 99%