Journal
ORGANIC LETTERS
Volume 23, Issue 12, Pages 4657-4661Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01393
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Funding
- NSFC [22071057, 21971065, 21871089]
- STCSM [20XD1421500, 20JC1416800, 18JC1415600]
- Innovative Research Team of High-Level Local Universities in Shanghai [SSMU-ZLCX20180501]
- Fundamental Research Funds for the Central Universities
- Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning
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The study successfully achieved a multicomponent reaction involving sodium dithionite for constructing alkyl and alkenyl tertiary sulfones. By utilizing sodium dithionite as a substitute and single-electron reductant, the decarboxylation of redox-active esters was initiated. Mechanistic studies revealed a proton trapping process in the transformation, distinct from the traditional radical trapping pathway.
A dithionite-involved multicomponent reaction of redox-active esters and alkenes/alkynes is comprehensively achieved for the construction of alkyl and alkenyl tertiary sulfones. The industrial feedstock sodium dithionite is employed as a sulfur dioxide surrogate and a single-electron reductant to initiate the decarboxylation of redox-active esters. Mechanistic studies further indicated that the transformation underwent a proton trapping process, which was different from the traditional radical trapping pathway.
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