Literature DB >> 21714533

Expedient synthesis of N-acyl anthranilamides and β-enamine amides by the Rh(III)-catalyzed amidation of aryl and vinyl C-H bonds with isocyanates.

Kevin D Hesp1, Robert G Bergman, Jonathan A Ellman.   

Abstract

A Rh(III)-catalyzed protocol for the amidation of anilide and enamide C-H bonds with isocyanates has been developed. This method provides direct and efficient syntheses of N-acyl anthranilamides, enamine amides, and pyrimidin-4-one heterocycles.

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Year:  2011        PMID： 21714533      PMCID： PMC3158987          DOI： 10.1021/ja203495c

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


  27 in total

1.  Rh(III)-catalyzed oxidative coupling of N-aryl-2-aminopyridine with alkynes and alkenes.

Authors:  Jinlei Chen; Guoyong Song; Cheng-Ling Pan; Xingwei Li
Journal:  Org Lett       Date:  2010-11-01       Impact factor: 6.005

2.  Oxidative coupling of aromatic substrates with alkynes and alkenes under rhodium catalysis.

Authors:  Tetsuya Satoh; Masahiro Miura
Journal:  Chemistry       Date:  2010-10-04       Impact factor: 5.236

3.  Rhodium-catalyzed direct addition of aryl C-H bonds to N-sulfonyl aldimines.

Authors:  Yang Li; Bi-Jie Li; Wen-Hua Wang; Wei-Ping Huang; Xi-Sha Zhang; Kang Chen; Zhang-Jie Shi
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-26       Impact factor: 15.336

4.  Rhodium(III)-catalyzed arylation of Boc-imines via C-H bond functionalization.

Authors:  Andy S Tsai; Michael E Tauchert; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2011-01-04       Impact factor: 15.419

5.  Pyrrole synthesis via allylic sp3 C-H activation of enamines followed by intermolecular coupling with unactivated alkynes.

Authors:  Souvik Rakshit; Frederic W Patureau; Frank Glorius
Journal:  J Am Chem Soc       Date:  2010-07-21       Impact factor: 15.419

6.  Rhodium(III)-catalyzed arene and alkene C-H bond functionalization leading to indoles and pyrroles.

Authors:  David R Stuart; Pamela Alsabeh; Michelle Kuhn; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2010-12-06       Impact factor: 15.419

7.  The vinyl moiety as a handle for regiocontrol in the preparation of unsymmetrical 2,3-aliphatic-substituted indoles and pyrroles.

Authors:  Malcolm P Huestis; Lina Chan; David R Stuart; Keith Fagnou
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-29       Impact factor: 15.336

8.  Synthesis of enamides via CuI-catalyzed reductive acylation of ketoximes with NaHSO3.

Authors:  Zheng-Hui Guan; Zhi-Yuan Zhang; Zhi-Hui Ren; Yao-Yu Wang; Xumu Zhang
Journal:  J Org Chem       Date:  2010-12-14       Impact factor: 4.354

9.  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

10.  Synthesis of aryl ketones by the PD-catalyzed C-H activation of arenes and intermolecular carbopalladation of nitriles.

Authors:  Chengxiang Zhou; Richard C Larock
Journal:  J Am Chem Soc       Date:  2004-03-03       Impact factor: 15.419
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  20 in total

1.  Rhodium catalyzed chelation-assisted C-H bond functionalization reactions.

Authors:  Denise A Colby; Andy S Tsai; Robert G Bergman; Jonathan A Ellman
Journal:  Acc Chem Res       Date:  2011-12-08       Impact factor: 22.384

2.  Rhodium(iii)-catalyzed synthesis of phthalides by cascade addition and cyclization of benzimidates with aldehydes.

Authors:  Yajing Lian; Robert G Bergman; Jonathan A Ellman
Journal:  Chem Sci       Date:  2012-08-02       Impact factor: 9.825

3.  Cobalt(III)-Catalyzed C-H Amidation of Dehydroalanine for the Site-Selective Structural Diversification of Thiostrepton.

Authors:  Ryan J Scamp; Edward deRamon; Eric K Paulson; Scott J Miller; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-27       Impact factor: 15.336

4.  Cobalt(III)-Catalyzed C-H Bond Amidation with Isocyanates.

Authors:  Joshua R Hummel; Jonathan A Ellman
Journal:  Org Lett       Date:  2015-05-06       Impact factor: 6.005

5.  Rhodium-catalyzed synthesis of branched amines by direct addition of benzamides to imines.

Authors:  Kevin D Hesp; Robert G Bergman; Jonathan A Ellman
Journal:  Org Lett       Date:  2012-04-13       Impact factor: 6.005

6.  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

7.  Transition-Metal-Catalyzed C-H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds.

Authors:  Joshua R Hummel; Jeffrey A Boerth; Jonathan A Ellman
Journal:  Chem Rev       Date:  2016-12-12       Impact factor: 60.622

8.  Efficient Benzimidazolidinone Synthesis via Rhodium-Catalyzed Double-Decarbonylative C-C Activation/Cycloaddition between Isatins and Isocyanates.

Authors:  Rong Zeng; Peng-Hao Chen; Guangbin Dong
Journal:  ACS Catal       Date:  2015-12-30       Impact factor: 13.084

9.  Palladium-catalyzed synthesis of N-aryl carbamates.

Authors:  Ekaterina V Vinogradova; Nathaniel H Park; Brett P Fors; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-02-26       Impact factor: 6.005

10.  Room temperature copper(II)-catalyzed oxidative cyclization of enamides to 2,5-disubstituted oxazoles via vinylic C-H functionalization.

Authors:  Chi Wai Cheung; Stephen L Buchwald
Journal:  J Org Chem       Date:  2012-08-13       Impact factor: 4.354
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