Literature DB >> 27603499

Generation of Sulfonyl Radicals from Aryldiazonium Tetrafluoroborates and Sulfur Dioxide: The Synthesis of 3-Sulfonated Coumarins.

Danqing Zheng1, Jiyao Yu2, Jie Wu3,4.   

Abstract

A catalyst-free approach for the generation of sulfonyl radicals from aryldiazonium tetrafluoroborates in the presence of DABCO⋅(SO2 )2 is realized. The combination of aryldiazonium tetrafluoroborates, DABCO⋅(SO2 )2 , and aryl propiolates affords 3-sulfonated coumarins in good to excellent yields. This tandem reaction process involves radical addition, spirocyclization, and 1,2-migration of esters. Additionally, the in situ diazotization of a number of anilines allows the directional synthesis of desired 3-sulfonated coumarins in a one-pot, two-step process.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  diazo compounds; heterocycles; radicals; sulfur; synthetic methods

Year:  2016        PMID： 27603499     DOI： 10.1002/anie.201607292

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


  6 in total

1.  Efficient synthesis of 3-sulfolenes from allylic alcohols and 1,3-dienes enabled by sodium metabisulfite as a sulfur dioxide equivalent.

Authors:  Hang T Dang; Vu T Nguyen; Viet D Nguyen; Hadi D Arman; Oleg V Larionov
Journal:  Org Biomol Chem       Date:  2018-05-15       Impact factor: 3.876

Review 2.  Recent Progress and Emerging Technologies towards a Sustainable Synthesis of Sulfones.

Authors:  Shuai Liang; Kamil Hofman; Marius Friedrich; Julian Keller; Georg Manolikakes
Journal:  ChemSusChem       Date:  2021-10-13       Impact factor: 9.140

3.  Sulfonylative and Azidosulfonylative Cyclizations by Visible-Light-Photosensitization of Sulfonyl Azides in THF.

Authors:  Shaoqun Zhu; Atchutarao Pathigoolla; Grace Lowe; Darren A Walsh; Mick Cooper; William Lewis; Hon Wai Lam
Journal:  Chemistry       Date:  2017-11-16       Impact factor: 5.236

4.  A computational study for the reaction mechanism of metal-free cyanomethylation of aryl alkynoates with acetonitrile.

Authors:  Selçuk Eşsiz
Journal:  RSC Adv       Date:  2021-05-20       Impact factor: 3.361

5.  Access to chiral β-sulfonyl carbonyl compounds via photoinduced organocatalytic asymmetric radical sulfonylation with sulfur dioxide.

Authors:  Fu-Sheng He; Chun Zhang; Minghui Jiang; Lujun Lou; Jie Wu; Shengqing Ye
Journal:  Chem Sci       Date:  2022-07-08       Impact factor: 9.969

6.  A mild light-induced cleavage of the S-O bond of aryl sulfonate esters enables efficient sulfonylation of vinylarenes.

Authors:  Maxim Ratushnyy; Monika Kamenova; Vladimir Gevorgyan
Journal:  Chem Sci       Date:  2018-07-25       Impact factor: 9.825
  6 in total

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