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Literature DB >> 25088979

Simple sulfinate synthesis enables C-H trifluoromethylcyclopropanation.

Ryan Gianatassio¹, Shuhei Kawamura, Cecil L Eprile, Klement Foo, Jason Ge, Aaron C Burns, Michael R Collins, Phil S Baran.

Abstract

A simple method to convert readily available carboxylic acids into sulfinate salts by employing an interrupted Barton decarboxylation reaction is reported. A medicinally oriented panel of ten new sulfinate reagents was created using this method, including a key trifluoromethylcyclopropanation reagent, TFCS-Na. The reactivity of six of these salts towards C-H functionalization was field-tested using several different classes of heterocycles.

Entities: Chemical Gene Species

Keywords: CH functionalization; analogue synthesis; bioisosteres; heterocycles; sulfinate salts

Mesh：

Substances：

Year: 2014 PMID： 25088979 PMCID： PMC4186797 DOI： 10.1002/anie.201406622

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

18 in total

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

Authors: Miles W Johnson; Scott W Bagley; Neal P Mankad; Robert G Bergman; Vincent Mascitti; F Dean Toste
Journal: Angew Chem Int Ed Engl Date: 2014-03-20 Impact factor: 15.336

2. Bioconjugation by native chemical tagging of C-H bonds.

Authors: Qianghui Zhou; Jinghan Gui; Chung-Mao Pan; Earl Albone; Xin Cheng; Edward M Suh; Luigi Grasso; Yoshihiro Ishihara; Phil S Baran
Journal: J Am Chem Soc Date: 2013-08-22 Impact factor: 15.419

3. Identification of a series of 4-[3-(quinolin-2-yl)-1,2,4-oxadiazol-5-yl]piperazinyl ureas as potent smoothened antagonist hedgehog pathway inhibitors.

Authors: Jesus M Ontoria; Laura Llauger Bufi; Caterina Torrisi; Alberto Bresciani; Claudia Giomini; Michael Rowley; Sergio Serafini; Hu Bin; Wu Hao; Christian Steinkühler; Philip Jones
Journal: Bioorg Med Chem Lett Date: 2011-07-14 Impact factor: 2.823

4. Metabolically Stable tert-Butyl Replacement.

Authors: David Barnes-Seeman; Monish Jain; Leslie Bell; Suzie Ferreira; Scott Cohen; Xiao-Hui Chen; Jakal Amin; Brad Snodgrass; Panos Hatsis
Journal: ACS Med Chem Lett Date: 2013-04-22 Impact factor: 4.345

5. 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

6. Synthesis and minisci reactions of organotrifluoroborato building blocks.

Authors: Marc Presset; Nicolas Fleury-Brégeot; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal: J Org Chem Date: 2013-04-17 Impact factor: 4.354

7. Aryloxazolidinediones: identification of potent orally active PPAR dual alpha/gamma agonists.

Authors: Ranjit C Desai; Dominick F Gratale; Wei Han; Hiroo Koyama; Edward Metzger; Victoria K Lombardo; Karen L MacNaul; Thomas W Doebber; Joel P Berger; Kwan Leung; Ronald Franklin; David E Moller; James V Heck; Soumya P Sahoo
Journal: Bioorg Med Chem Lett Date: 2003-10-20 Impact factor: 2.823

8. Benzodioxoles: novel cannabinoid-1 receptor inverse agonists for the treatment of obesity.

Authors: Leo Alig; Jochem Alsenz; Mirjana Andjelkovic; Stefanie Bendels; Agnès Bénardeau; Konrad Bleicher; Anne Bourson; Pascale David-Pierson; Wolfgang Guba; Stefan Hildbrand; Dagmar Kube; Thomas Lübbers; Alexander V Mayweg; Robert Narquizian; Werner Neidhart; Matthias Nettekoven; Jean-Marc Plancher; Cynthia Rocha; Mark Rogers-Evans; Stephan Röver; Gisbert Schneider; Sven Taylor; Pius Waldmeier
Journal: J Med Chem Date: 2008-03-13 Impact factor: 7.446

9. Practical method for the Cu-mediated trifluoromethylation of arylboronic acids with CF3 radicals derived from NaSO2CF3 and tert-butyl hydroperoxide (TBHP).

Authors: Yingda Ye; Stefan A Künzi; Melanie S Sanford
Journal: Org Lett Date: 2012-09-17 Impact factor: 6.005

10. Direct synthesis of fluorinated heteroarylether bioisosteres.

Authors: Qianghui Zhou; Alessandro Ruffoni; Ryan Gianatassio; Yuta Fujiwara; Eran Sella; Doron Shabat; Phil S Baran
Journal: Angew Chem Int Ed Engl Date: 2013-03-04 Impact factor: 15.336

20 in total

1. Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters.

Authors: Sébastien Laulhé; J Miles Blackburn; Jennifer L Roizen
Journal: Chem Commun (Camb) Date: 2017-06-29 Impact factor: 6.222

2. Late-Stage C-H Alkylation of Heterocycles and 1,4-Quinones via Oxidative Homolysis of 1,4-Dihydropyridines.

Authors: Álvaro Gutiérrez-Bonet; Camille Remeur; Jennifer K Matsui; Gary A Molander
Journal: J Am Chem Soc Date: 2017-08-23 Impact factor: 15.419

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 Retrosynthesis.

Authors: Joel M Smith; Stephen J Harwood; Phil S Baran
Journal: Acc Chem Res Date: 2018-08-02 Impact factor: 22.384

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

6. Fluorine-decoupled carbon spectroscopy for the determination of configuration at fully substituted, trifluoromethyl- and perfluoroalkyl-bearing carbons: comparison with 19F-1H heteronuclear Overhauser effect spectroscopy.

Authors: Appi Reddy Mandhapati; Takayuki Kato; Takahiko Matsushita; Bashar Ksebati; Andrea Vasella; Erik C Böttger; David Crich
Journal: J Org Chem Date: 2015-01-20 Impact factor: 4.354

Simple sulfinate synthesis enables C-H trifluoromethylcyclopropanation.

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

2. Bioconjugation by native chemical tagging of C-H bonds.

3. Identification of a series of 4-[3-(quinolin-2-yl)-1,2,4-oxadiazol-5-yl]piperazinyl ureas as potent smoothened antagonist hedgehog pathway inhibitors.

4. Metabolically Stable tert-Butyl Replacement.

5. A new reagent for direct difluoromethylation.

6. Synthesis and minisci reactions of organotrifluoroborato building blocks.

7. Aryloxazolidinediones: identification of potent orally active PPAR dual alpha/gamma agonists.

8. Benzodioxoles: novel cannabinoid-1 receptor inverse agonists for the treatment of obesity.

9. Practical method for the Cu-mediated trifluoromethylation of arylboronic acids with CF3 radicals derived from NaSO2CF3 and tert-butyl hydroperoxide (TBHP).

10. Direct synthesis of fluorinated heteroarylether bioisosteres.

1. Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters.

2. Late-Stage C-H Alkylation of Heterocycles and 1,4-Quinones via Oxidative Homolysis of 1,4-Dihydropyridines.

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

4. Radical Retrosynthesis.

5. Academia-industry symbiosis in organic chemistry.

6. Fluorine-decoupled carbon spectroscopy for the determination of configuration at fully substituted, trifluoromethyl- and perfluoroalkyl-bearing carbons: comparison with 19F-1H heteronuclear Overhauser effect spectroscopy.

Review 7. Radicals: Reactive Intermediates with Translational Potential.

Review 8. Synthetic Organic Electrochemistry: An Enabling and Innately Sustainable Method.

9. Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters.

10. Sultones and Sultines via a Julia-Kocienski Reaction of Epoxides.

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

Review 7. Radicals: Reactive Intermediates with Translational Potential.

Review 8. Synthetic Organic Electrochemistry: An Enabling and Innately Sustainable Method.

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