In this study, we report a novel and efficient one-pot synthesis of mixed phosphorotrithioates under mild conditions at ambient temperature, obviating the requirement for supplementary additives. The method's versatility stems from its utilization of diverse thiols as nucleophilic reactants, 1-chloro-,,','-tetraisopropylphosphanediamine [bis(diisopropylamino)chlorophosphine] as the phosphorus precursor, and various sulphenyl chlorides as sources of electrophilic sulfur. Notably, our investigation extends beyond mixed phosphorotrithioates to encompass the synthesis of phosphoroselenodithioates, underscoring the broad applicability of this synthetic protocol.
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http://dx.doi.org/10.1039/d3ob01668d | DOI Listing |
Org Biomol Chem
March 2024
Natural Product and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu-180001, India.
Herein, we present the first, one-step, direct synthesis of unsymmetric phosphorotrithioates through a process involving sequential coupling of 1,1-dichloro-,-diethylphosphanamine with thiols and sulfenyl chloride. This method showcases excellent functional group tolerance, substrate compatibility, and mild reaction conditions, offering a streamlined approach for the challenging phosphorotrithioate synthesis. Additionally, the applicability of this method can be extended to the synthesis of mixed phosphoroselenodithioates.
View Article and Find Full Text PDFOrg Biomol Chem
January 2024
Natural Product and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu-180001, India.
In this study, we report a novel and efficient one-pot synthesis of mixed phosphorotrithioates under mild conditions at ambient temperature, obviating the requirement for supplementary additives. The method's versatility stems from its utilization of diverse thiols as nucleophilic reactants, 1-chloro-,,','-tetraisopropylphosphanediamine [bis(diisopropylamino)chlorophosphine] as the phosphorus precursor, and various sulphenyl chlorides as sources of electrophilic sulfur. Notably, our investigation extends beyond mixed phosphorotrithioates to encompass the synthesis of phosphoroselenodithioates, underscoring the broad applicability of this synthetic protocol.
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