Literature DB >> 23477353

Sulfoximine directed intermolecular o-C-H amidation of arenes with sulfonyl azides.

M Ramu Yadav1, Raja K Rit, Akhila K Sahoo.   

Abstract

The Ru(II)-catalyzed intermolecular o-C-H amidation of arenes in N-benzoylated sulfoximine with sulfonyl azides is demonstrated. The reaction proceeds with broad substrate scope and tolerates various functional groups. Base hydrolysis of the amidation product provides the anthranilic acid derivatives and methylphenyl sulfoximine (MPS) directing group. This method is successfully employed for the synthesis of HMR 1766.

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Year:  2013        PMID: 23477353     DOI: 10.1021/ol400411v

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  Facile synthesis of unsymmetrical acridines and phenazines by a Rh(III)-catalyzed amination/cyclization/aromatization cascade.

Authors:  Yajing Lian; Joshua R Hummel; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2013-08-19       Impact factor: 15.419

Review 2.  Synthesis and Transformations of NH-Sulfoximines.

Authors:  Michael Andresini; Arianna Tota; Leonardo Degennaro; James A Bull; Renzo Luisi
Journal:  Chemistry       Date:  2021-10-13       Impact factor: 5.020

Review 3.  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

4.  In situ generation of N-unsubstituted imines from alkyl azides and their applications for imine transfer via copper catalysis.

Authors:  Lu Hu; Yahu A Liu; Xuebin Liao
Journal:  Sci Adv       Date:  2017-08-09       Impact factor: 14.136

5.  Iridium-catalyzed ortho-selective carbon-hydrogen amidation of benzamides with sulfonyl azides in ionic liquid.

Authors:  Lin-Yu Jiao; Zi-Hui Ning; Qian Hong; Xin-Hua Peng; Xiao-Mei Yin; Shanshan Liu; Huiyong Chen; Zhuo Li; Ming Sun; Xiao-Xun Ma
Journal:  RSC Adv       Date:  2020-08-11       Impact factor: 3.361

Review 6.  Direct sulfonamidation of (hetero)aromatic C-H bonds with sulfonyl azides: a novel and efficient route to N-(hetero)aryl sulfonamides.

Authors:  Zhi Liu; Abdolghaffar Ebadi; Mohsen Toughani; Nihat Mert; Esmail Vessally
Journal:  RSC Adv       Date:  2020-10-08       Impact factor: 4.036

  6 in total

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