Literature DB >> 23640168

Preparation and purification of zinc sulfinate reagents for drug discovery.

Fionn O'Hara1, Ryan D Baxter, Alexander G O'Brien, Michael R Collins, Janice A Dixon, Yuta Fujiwara, Yoshihiro Ishihara, Phil S Baran.   

Abstract

The present protocol details the synthesis of zinc bis(alkanesulfinate)s that can be used as general reagents for the formation of radical species. The zinc sulfinates described herein are generated from the corresponding sulfonyl chlorides by treatment with zinc dust. The products may be used crude, or a simple purification procedure may be performed to minimize incorporation of water and zinc chloride. Although the synthesis of the zinc sulfinate salts can generally be completed within 3 h, workup can take up to 24 h and purification can take up to 3 h. Following the steps in this protocol would enable the user to generate a small toolkit of zinc sulfinate reagents over the course of 1 week.

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Year:  2013        PMID: 23640168      PMCID: PMC4114315          DOI: 10.1038/nprot.2013.059

Source DB:  PubMed          Journal:  Nat Protoc        ISSN: 1750-2799            Impact factor:   13.491


  5 in total

1.  Innate and guided C-H functionalization logic.

Authors:  Tobias Brückl; Ryan D Baxter; Yoshihiro Ishihara; Phil S Baran
Journal:  Acc Chem Res       Date:  2011-10-21       Impact factor: 22.384

2.  Innate C-H trifluoromethylation of heterocycles.

Authors:  Yining Ji; Tobias Brueckl; Ryan D Baxter; Yuta Fujiwara; Ian B Seiple; Shun Su; Donna G Blackmond; Phil S Baran
Journal:  Proc Natl Acad Sci U S A       Date:  2011-08-15       Impact factor: 11.205

3.  A new reagent for direct difluoromethylation.

Authors:  Yuta Fujiwara; Janice A Dixon; Rodrigo A Rodriguez; Ryan D Baxter; Darryl D Dixon; Michael R Collins; Donna G Blackmond; Phil S Baran
Journal:  J Am Chem Soc       Date:  2012-01-13       Impact factor: 15.419

4.  Copper- and iron-catalyzed decarboxylative tri- and difluoromethylation of α,β-unsaturated carboxylic acids with CF3SO2Na and (CF2HSO2)2Zn via a radical process.

Authors:  Zejiang Li; Zili Cui; Zhong-Quan Liu
Journal:  Org Lett       Date:  2013-01-10       Impact factor: 6.005

5.  Practical and innate carbon-hydrogen functionalization of heterocycles.

Authors:  Yuta Fujiwara; Janice A Dixon; Fionn O'Hara; Erik Daa Funder; Darryl D Dixon; Rodrigo A Rodriguez; Ryan D Baxter; Bart Herlé; Neal Sach; Michael R Collins; Yoshihiro Ishihara; Phil S Baran
Journal:  Nature       Date:  2012-11-28       Impact factor: 49.962

  5 in total
  7 in total

1.  Radical-based regioselective C-H functionalization of electron-deficient heteroarenes: scope, tunability, and predictability.

Authors:  Fionn O'Hara; Donna G Blackmond; Phil S Baran
Journal:  J Am Chem Soc       Date:  2013-07-30       Impact factor: 15.419

2.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

Review 3.  Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds.

Authors:  Raju Jannapu Reddy; Arram Haritha Kumari
Journal:  RSC Adv       Date:  2021-03-01       Impact factor: 3.361

4.  Radical C-H functionalization of heteroarenes under electrochemical control.

Authors:  Alexander G O'Brien; Akinobu Maruyama; Yasuhide Inokuma; Makoto Fujita; Phil S Baran; Donna G Blackmond
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-10       Impact factor: 15.336

5.  Academia-industry symbiosis in organic chemistry.

Authors:  Quentin Michaudel; Yoshihiro Ishihara; Phil S Baran
Journal:  Acc Chem Res       Date:  2015-02-23       Impact factor: 22.384

Review 6.  Radicals: Reactive Intermediates with Translational Potential.

Authors:  Ming Yan; Julian C Lo; Jacob T Edwards; Phil S Baran
Journal:  J Am Chem Soc       Date:  2016-09-26       Impact factor: 15.419

7.  A practical and catalyst-free trifluoroethylation reaction of amines using trifluoroacetic acid.

Authors:  Keith G Andrews; Radmila Faizova; Ross M Denton
Journal:  Nat Commun       Date:  2017-06-26       Impact factor: 14.919

  7 in total

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