Literature DB >> 34161084

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

Patrick J Sarver1, Noah B Bissonnette1, David W C MacMillan1.   

Abstract

Here we report the direct conversion of strong, aliphatic C(sp3)-H bonds into the corresponding alkyl sulfinic acids via decatungstate photocatalysis. This transformation has been applied to a diverse range of C(sp3)-rich scaffolds, including natural products and approved pharmaceuticals, providing efficient access to complex sulfur-containing products. To demonstrate the broad potential of this methodology for the divergent synthesis of pharmaceutically relevant molecules, procedures for the diversification of the sulfinic acid products into a range of medicinally relevant functional groups have been developed.

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Year:  2021        PMID: 34161084      PMCID: PMC8627221          DOI: 10.1021/jacs.1c04722

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  45 in total

1.  Photocatalysis. A multi-faceted concept for green chemistry.

Authors:  Davide Ravelli; Daniele Dondi; Maurizio Fagnoni; Angelo Albini
Journal:  Chem Soc Rev       Date:  2009-04-21       Impact factor: 54.564

2.  Platinum-Catalyzed, Terminal-Selective C(sp(3))-H Oxidation of Aliphatic Amines.

Authors:  Melissa Lee; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2015-10-06       Impact factor: 15.419

3.  DABCO-bis(sulfur dioxide), DABSO, as a convenient source of sulfur dioxide for organic synthesis: utility in sulfonamide and sulfamide preparation.

Authors:  Holly Woolven; Carlos González-Rodríguez; Isabel Marco; Amber L Thompson; Michael C Willis
Journal:  Org Lett       Date:  2011-08-25       Impact factor: 6.005

4.  Coupling Reaction between Aldehydes and Non-Activated Hydrocarbons via the Reductive Radical-Polar Crossover Pathway.

Authors:  Kenzo Yahata; Shu Sakurai; Shuhei Hori; Shin Yoshioka; Yuki Kaneko; Kai Hasegawa; Shuji Akai
Journal:  Org Lett       Date:  2020-01-15       Impact factor: 6.005

Review 5.  Sulfinate derivatives: dual and versatile partners in organic synthesis.

Authors:  Jessy Aziz; Samir Messaoudi; Mouad Alami; Abdallah Hamze
Journal:  Org Biomol Chem       Date:  2014-12-28       Impact factor: 3.876

Review 6.  An update on the use of sulfinate derivatives as versatile coupling partners in organic chemistry.

Authors:  Jessy Aziz; Abdallah Hamze
Journal:  Org Biomol Chem       Date:  2020-11-25       Impact factor: 3.876

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

Authors:  Yaping Li; Shihao Chen; Ming Wang; Xuefeng Jiang
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-25       Impact factor: 15.336

8.  Multicomponent Reductive Cross-Coupling of an Inorganic Sulfur Dioxide Surrogate: Straightforward Construction of Diversely Functionalized Sulfones.

Authors:  Yingying Meng; Ming Wang; Xuefeng Jiang
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-29       Impact factor: 15.336

9.  Direct arylation of strong aliphatic C-H bonds.

Authors:  Ian B Perry; Thomas F Brewer; Patrick J Sarver; Danielle M Schultz; Daniel A DiRocco; David W C MacMillan
Journal:  Nature       Date:  2018-08-01       Impact factor: 49.962

10.  Photocatalytic three-component asymmetric sulfonylation via direct C(sp3)-H functionalization.

Authors:  Shi Cao; Wei Hong; Ziqi Ye; Lei Gong
Journal:  Nat Commun       Date:  2021-04-22       Impact factor: 14.919

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  7 in total

1.  Radical C(sp3)-H functionalization and cross-coupling reactions.

Authors:  Dung L Golden; Sung-Eun Suh; Shannon S Stahl
Journal:  Nat Rev Chem       Date:  2022-05-17       Impact factor: 34.571

2.  Decatungstate-catalyzed radical disulfuration through direct C-H functionalization for the preparation of unsymmetrical disulfides.

Authors:  Jingjing Zhang; Armido Studer
Journal:  Nat Commun       Date:  2022-07-06       Impact factor: 17.694

3.  Decatungstate-photocatalysed C(sp3)-H azidation.

Authors:  Yen-Chu Lu; Shih-Chieh Kao; Julian G West
Journal:  Chem Commun (Camb)       Date:  2022-04-14       Impact factor: 6.065

4.  Membrane-based TBADT recovery as a strategy to increase the sustainability of continuous-flow photocatalytic HAT transformations.

Authors:  Zhenghui Wen; Diego Pintossi; Manuel Nuño; Timothy Noël
Journal:  Nat Commun       Date:  2022-10-18       Impact factor: 17.694

5.  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

6.  Accelerated and Scalable C(sp3)-H Amination via Decatungstate Photocatalysis Using a Flow Photoreactor Equipped with High-Intensity LEDs.

Authors:  Ting Wan; Zhenghui Wen; Gabriele Laudadio; Luca Capaldo; Rob Lammers; Juan A Rincón; Pablo García-Losada; Carlos Mateos; Michael O Frederick; Rémy Broersma; Timothy Noël
Journal:  ACS Cent Sci       Date:  2021-12-16       Impact factor: 14.553

Review 7.  Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration.

Authors:  Luca Capaldo; Davide Ravelli; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2021-08-06       Impact factor: 60.622

  7 in total

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