Literature DB >> 22006288

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

Ya Du1, Todd K Hyster, Tomislav Rovis.   

Abstract

An efficient strategy for the oxidative carbonylation of aromatic amides via C-H/N-H activation to form phthalimides using an Rh(III) catalyst has been developed. The reaction shows a preference for C-H bonds of electron-rich aromatic amides and tolerates a variety of functional groups.

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 22006288      PMCID： PMC3423973          DOI： 10.1039/c1cc15843k

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


  16 in total

1.  A More Efficient Catalyst for the Carbonylation of Chloroarenes Palladium-Catalyzed Reactions for Fine Chemical Synthesis, Part 19. This project was suported by the Solvias AG, Basel (Switzerland), and from the Bildungsministerium des Landes Mecklenburg-Vorpommern. We thank Dres. H.-U. Blaser, M. Studer, A. Schnyder, and F. Spindler (Solvias AG) for helpful contributions, M. Heyken (IfOK) for technical support, and Dr. C. Fischer, K. Kortus, and S. Buchholz (IfOK) for analytical work. Part 18: ref.

Authors:  Wolfgang Mägerlein; Adriano F. Indolese; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2001-08-03       Impact factor: 15.336

2.  Rh-catalyzed oxidative coupling between primary and secondary benzamides and alkynes: synthesis of polycyclic amides.

Authors:  Guoyong Song; Dan Chen; Cheng-Ling Pan; Robert H Crabtree; Xingwei Li
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

3.  The dienyl Pauson-Khand reaction.

Authors:  Paul A Wender; Nicole M Deschamps; Gabriel G Gamber
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-25       Impact factor: 15.336

4.  Synthesis of 1,2- and 1,3-dicarboxylic acids via Pd(II)-catalyzed carboxylation of aryl and vinyl C-H bonds.

Authors:  Ramesh Giri; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2008-10-04       Impact factor: 15.419

5.  An Improved Catalyst Architecture for Rhodium (III) Catalyzed C-H Activation and its Application to Pyridone Synthesis.

Authors:  Todd K Hyster; Tomislav Rovis
Journal:  Chem Sci       Date:  2011-08-01       Impact factor: 9.825

6.  Rhodium-catalyzed oxidative cycloaddition of benzamides and alkynes via C-H/N-H activation.

Authors:  Todd K Hyster; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2010-08-04       Impact factor: 15.419

7.  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

8.  Palladium-catalyzed oxidative carbonylation of alkyl and aryl indium reagents with CO under mild conditions.

Authors:  Yingsheng Zhao; Liqun Jin; Peng Li; Aiwen Lei
Journal:  J Am Chem Soc       Date:  2008-06-25       Impact factor: 15.419

9.  Synthetic studies and mechanistic insight in nickel-catalyzed [4+2+1] cycloadditions.

Authors:  Yike Ni; John Montgomery
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

10.  Ruthenium-catalyzed carbonylation at ortho C-H bonds in aromatic amides leading to phthalimides: C-H bond activation utilizing a bidentate system.

Authors:  Satoshi Inoue; Hirotaka Shiota; Yoshiya Fukumoto; Naoto Chatani
Journal:  J Am Chem Soc       Date:  2009-05-27       Impact factor: 15.419
View more
  15 in total

1.  Correlating Reactivity and Selectivity to Cyclopentadienyl Ligand Properties in Rh(III)-Catalyzed C-H Activation Reactions: An Experimental and Computational Study.

Authors:  Tiffany Piou; Fedor Romanov-Michailidis; Maria Romanova-Michaelides; Kelvin E Jackson; Natthawat Semakul; Trevor D Taggart; Brian S Newell; Christopher D Rithner; Robert S Paton; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2017-01-06       Impact factor: 15.419

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

Authors:  Tung Thanh Nguyen; Liene Grigorjeva; Olafs Daugulis
Journal:  Chem Commun (Camb)       Date:  2017-05-04       Impact factor: 6.222

Review 3.  Electronic and Steric Tuning of a Prototypical Piano Stool Complex: Rh(III) Catalysis for C-H Functionalization.

Authors:  Tiffany Piou; Tomislav Rovis
Journal:  Acc Chem Res       Date:  2017-12-22       Impact factor: 22.384

4.  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

5.  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

6.  A coupling of benzamides and donor/acceptor diazo compounds to form γ-lactams via Rh(III)-catalyzed C-H activation.

Authors:  Todd K Hyster; Kyle E Ruhl; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2013-04-02       Impact factor: 15.419

7.  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

8.  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

9.  Mechanism of the rhodium(III)-catalyzed arylation of imines via C-H bond functionalization: inhibition by substrate.

Authors:  Michael E Tauchert; Christopher D Incarvito; Arnold L Rheingold; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2012-01-17       Impact factor: 15.419

10.  Rhodium(III)-catalyzed alkenyl C-H bond functionalization: convergent synthesis of furans and pyrroles.

Authors:  Yajing Lian; Tatjana Huber; Kevin D Hesp; Robert G Bergman; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-22       Impact factor: 15.336
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.