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Literature DB >> 24652820

Application of fundamental organometallic chemistry to the development of a gold-catalyzed synthesis of sulfinate derivatives.

Miles W Johnson¹, Scott W Bagley, Neal P Mankad, Robert G Bergman, Vincent Mascitti, F Dean Toste.

Abstract

The development of a gold(I)-catalyzed sulfination of aryl boronic acids is described. This transformation proceeds through an unprecedented mechanism which exploits the reactivity of gold(I)-heteroatom bonds to form sulfinate anions. Further in situ elaboration of the sulfinate intermediates leads to the corresponding sulfones and sulfonamides, two pharmacophores routinely encountered in drug discovery.

Entities: Chemical Gene

Keywords: gold; heterocycles; structure elucidation; sulfonamides; synthetic methods

Mesh：

Substances：

Year: 2014 PMID： 24652820 PMCID： PMC5089845 DOI： 10.1002/anie.201400037

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

14 in total

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2. A palladium-catalyzed three-component coupling of arylboronic acids, sulfur dioxide and hydrazines.

Authors: Shengqing Ye; Jie Wu
Journal: Chem Commun (Camb) Date: 2012-06-29 Impact factor: 6.222

3. Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids.

Authors: J Robb DeBergh; Nootaree Niljianskul; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2013-07-12 Impact factor: 15.419

4. Palladium-catalyzed sulfination of aryl and heteroaryl halides: direct access to sulfones and sulfonamides.

Authors: Andrei Shavnya; Steven B Coffey; Aaron C Smith; Vincent Mascitti
Journal: Org Lett Date: 2013-11-20 Impact factor: 6.005

5. A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors: Nathan D Shapiro; F Dean Toste
Journal: Synlett Date: 2010-03-01 Impact factor: 2.454

6. Gold-catalyzed three-component coupling: oxidative oxyarylation of alkenes.

Authors: Asa D Melhado; William E Brenzovich; Aaron D Lackner; F Dean Toste
Journal: J Am Chem Soc Date: 2010-07-07 Impact factor: 15.419

7. Homogeneous gold-catalyzed oxidative carboheterofunctionalization of alkenes.

Authors: Guozhu Zhang; Li Cui; Yanzhao Wang; Liming Zhang
Journal: J Am Chem Soc Date: 2010-02-10 Impact factor: 15.419

8. Palladium-catalyzed aminosulfonylation of aryl halides.

Authors: Bao Nguyen; Edward J Emmett; Michael C Willis
Journal: J Am Chem Soc Date: 2010-10-28 Impact factor: 15.419

9. Copper-catalyzed sulfonamides formation from sodium sulfinates and amines.

Authors: Xiaodong Tang; Liangbin Huang; Chaorong Qi; Xia Wu; Wanqing Wu; Huanfeng Jiang
Journal: Chem Commun (Camb) Date: 2013-07-11 Impact factor: 6.222

10. Design, synthesis and biological evaluation of Trypanosoma brucei trypanothione synthetase inhibitors.

Authors: Daniel Spinks; Leah S Torrie; Stephen Thompson; Justin R Harrison; Julie A Frearson; Kevin D Read; Alan H Fairlamb; Paul G Wyatt; Ian H Gilbert
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15 in total

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2. Simple sulfinate synthesis enables C-H trifluoromethylcyclopropanation.

Authors: Ryan Gianatassio; Shuhei Kawamura; Cecil L Eprile; Klement Foo; Jason Ge; Aaron C Burns; Michael R Collins; Phil S Baran
Journal: Angew Chem Int Ed Engl Date: 2014-08-03 Impact factor: 15.336

3. Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate.

Authors: James R Colombe; J Robb DeBergh; Stephen L Buchwald
Journal: Org Lett Date: 2015-06-11 Impact factor: 6.005

4. One-pot, three-component arylalkynyl sulfone synthesis.

Authors: C Chun Chen; Jerome Waser
Journal: Org Lett Date: 2015-01-29 Impact factor: 6.005

5. Migratory Insertion of Carbenes into Au(III)-C Bonds.

Authors: Aleksandr V Zhukhovitskiy; Ilia J Kobylianskii; Chung-Yeh Wu; F Dean Toste
Journal: J Am Chem Soc Date: 2017-12-20 Impact factor: 15.419

6. Copper(i)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling.

Authors: Yiding Chen; Michael C Willis
Journal: Chem Sci Date: 2017-02-28 Impact factor: 9.825

7. One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides.

Authors: Alyn T Davies; John M Curto; Scott W Bagley; Michael C Willis
Journal: Chem Sci Date: 2016-10-11 Impact factor: 9.825

8. An efficient approach for the synthesis of novel methyl sulfones in acetic acid medium and evaluation of antimicrobial activity.

Authors: Gollapudi Ravi Kumar; Chandra Rao Dasireddy; Ravi Varala; Vijay Kotra; Hari Babu Bollikolla
Journal: Turk J Chem Date: 2020-10-26 Impact factor: 1.239

9. Palladium(II)-Catalyzed Synthesis of Sulfinates from Boronic Acids and DABSO: A Redox-Neutral, Phosphine-Free Transformation.

Authors: Alex S Deeming; Claire J Russell; Michael C Willis
Journal: Angew Chem Int Ed Engl Date: 2015-11-24 Impact factor: 15.336

10. Cross-Coupling of Sodium Sulfinates with Aryl, Heteroaryl, and Vinyl Halides by Nickel/Photoredox Dual Catalysis.

Authors: Huifeng Yue; Chen Zhu; Magnus Rueping
Journal: Angew Chem Int Ed Engl Date: 2018-01-05 Impact factor: 15.336