Literature DB >> 32149440

Sodium Dithionite-Mediated Decarboxylative Sulfonylation: Facile Access to Tertiary Sulfones.

Yaping Li1, Shihao Chen1, Ming Wang1, Xuefeng Jiang1,2,3.   

Abstract

A straightforward multicomponent decarboxylative cross coupling of redox-active esters (N-hydroxyphthalimide ester), sodium dithionite, and electrophiles was established to construct sterically bulky sulfones. The inorganic salt sodium dithionite not only served as the sulfur dioxide source, but also acted as an efficient radical initiator for the decarboxylation. Notably, diverse naturally abundant carboxylic acids and artificially prepared carboxyl-containing drugs with multiple heteroatoms and sensitive functional groups successfully underwent this decarboxylative sulfonylation to provide sterically bulky tertiary sulfones. Mechanistic studies further demonstrated that decarboxylation was the rate-determining step and occurred via a single-electron transfer (SET) process with the assistance of sodium dithionite.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  decarboxylative cross coupling; radicals; sodium dithionite; sulfones; sulfur dioxide

Year:  2020        PMID: 32149440     DOI: 10.1002/anie.202001589

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  5 in total

1.  Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides.

Authors:  Vu T Nguyen; Graham C Haug; Viet D Nguyen; Ngan T H Vuong; Hadi D Arman; Oleg V Larionov
Journal:  Chem Sci       Date:  2021-04-13       Impact factor: 9.825

2.  Functional group divergence and the structural basis of acridine photocatalysis revealed by direct decarboxysulfonylation.

Authors:  Vu T Nguyen; Graham C Haug; Viet D Nguyen; Ngan T H Vuong; Guna B Karki; Hadi D Arman; Oleg V Larionov
Journal:  Chem Sci       Date:  2022-03-21       Impact factor: 9.825

Review 3.  (Hetero)aryl-SVI Fluorides: Synthetic Development and Opportunities.

Authors:  Marc Magre; Shengyang Ni; Josep Cornella
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-27       Impact factor: 16.823

4.  Visible-Light-Mediated Three-Component Cascade Sulfonylative Annulation.

Authors:  Ganesh Chandra Upreti; Tavinder Singh; Sudhir Ranjan; Raju Kumar Gupta; Anand Singh
Journal:  ACS Omega       Date:  2022-08-18

5.  Decatungstate-Catalyzed C(sp3)-H Sulfinylation: Rapid Access to Diverse Organosulfur Functionality.

Authors:  Patrick J Sarver; Noah B Bissonnette; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2021-06-23       Impact factor: 15.419

  5 in total

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