Literature DB >> 28443897

Aminoquinoline-directed, cobalt-catalyzed carbonylation of sulfonamide sp2 C-H bonds.

Tung Thanh Nguyen1, Liene Grigorjeva, Olafs Daugulis.   

Abstract

We report a method for cobalt-catalyzed, aminoquinoline-directed sp2 C-H bond carbonylation of sulfonamides. The reactions proceed in a dichloroethane solvent, and employ diisopropyl azodicarboxylate as a carbon monoxide source, Mn(OAc)2 as a cooxidant and potassium pivalate as a base. Halogen, ester, and amide functionalities are compatible with the reaction conditions. This method allows for a short and efficient synthesis of saccharin derivatives.

Entities:  

Year:  2017        PMID： 28443897      PMCID： PMC5710005          DOI： 10.1039/c7cc02062g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  39 in total

1.  Rhodium(III)-catalyzed oxidative carbonylation of benzamides with carbon monoxide.

Authors:  Ya Du; Todd K Hyster; Tomislav Rovis
Journal:  Chem Commun (Camb)       Date:  2011-10-17       Impact factor: 6.222

2.  C-H functionalization logic in total synthesis.

Authors:  Will R Gutekunst; Phil S Baran
Journal:  Chem Soc Rev       Date:  2011-02-07       Impact factor: 54.564

3.  Effect of thalidomide-derivatives on limb development in culture.

Authors:  D Neubert; R Krowke
Journal:  Prog Clin Biol Res       Date:  1983

4.  Chiral Cyclopentadienyls: Enabling Ligands for Asymmetric Rh(III)-Catalyzed C-H Functionalizations.

Authors:  Baihua Ye; Nicolai Cramer
Journal:  Acc Chem Res       Date:  2015-04-17       Impact factor: 22.384

5.  Synthetic applications of Pd(II)-catalyzed C-H carboxylation and mechanistic insights: expedient routes to anthranilic acids, oxazolinones, and quinazolinones.

Authors:  Ramesh Giri; Jonathan K Lam; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-01-20       Impact factor: 15.419

6.  Modifying 5-HT1A Receptor Gene Expression as a New Target for Antidepressant Therapy.

Authors:  Paul R Albert; Brice Le François
Journal:  Front Neurosci       Date:  2010-06-17       Impact factor: 4.677

7.  Rhodium-catalyzed direct oxidative carbonylation of aromatic C-H bond with CO and alcohols.

Authors:  Zheng-Hui Guan; Zhi-Hui Ren; Stephen M Spinella; Shichao Yu; Yong-Min Liang; Xumu Zhang
Journal:  J Am Chem Soc       Date:  2009-01-21       Impact factor: 15.419

8.  Copper-Catalyzed Intramolecular Benzylic C-H Amination for the Synthesis of Isoindolinones.

Authors:  Chiaki Yamamoto; Kazutaka Takamatsu; Koji Hirano; Masahiro Miura
Journal:  J Org Chem       Date:  2016-08-18       Impact factor: 4.354

9.  Cobalt-Catalyzed Carbonylation of C(sp2)-H Bonds with Azodicarboxylate as the Carbonyl Source.

Authors:  Jiabin Ni; Jie Li; Zhoulong Fan; Ao Zhang
Journal:  Org Lett       Date:  2016-11-08       Impact factor: 6.005

10.  Cobalt-catalyzed direct carbonylation of aminoquinoline benzamides.

Authors:  Liene Grigorjeva; Olafs Daugulis
Journal:  Org Lett       Date:  2014-08-22       Impact factor: 6.005
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  3 in total

1.  Cobalt-Catalyzed Coupling of Benzoic Acid C-H Bonds with Alkynes, Styrenes, and 1,3-Dienes.

Authors:  Tung Thanh Nguyen; Liene Grigorjeva; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-10       Impact factor: 15.336

Review 2.  A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors:  Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal:  Chem Soc Rev       Date:  2018-08-28       Impact factor: 54.564

3.  Switching the site-selectivity of C-H activation in aryl sulfonamides containing strongly coordinating N-heterocycles.

Authors:  Yi Dong; XuePeng Zhang; Jiajing Chen; Wenxing Zou; Songwen Lin; Heng Xu
Journal:  Chem Sci       Date:  2019-08-12       Impact factor: 9.825
  3 in total

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