Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 48, Pages 6983-6990Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201801393
Keywords
Synthesis design; Domino reactions; COS; Benzothiazolone derivatives; Reaction mechanisms
Categories
Funding
- National Natural Science Foundation of China [21362019, 21865020]
- Natural Science Foundation of Inner Mongolia Autonomous Region of China [2016MS0207]
- CAS Light of West China Program
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Carbonyl sulfide (COS), whose molecular structure is similar to CO2 and CS2, could be used as a better alternative carbonyl reagent due to its high chemical activity. However, the unfriendly by-product H2S would be generated when COS is used as a carbonyl reagent in the carbonylation reaction. In this report, the odorless and stable disulfide was used to replace the traditional foul smelling and unstable o-aminobenzenethiol to react with COS for preparing benzothiazolone derivatives in excellent yield, in which coupling reaction of H2S generation and S-S bond cleavage was firstly designed. Notably, the C=O of COS was converted into benzothiazolone derivatives by carbonylation reaction and the sulfur of COS was transformed into sulfur and sulfide after cleaving the S-S bond by a domino reaction of disulfide and COS under mild conditions. This efficient synthetic methodology provided a promising process for the utilization of COS.
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