Literature DB >> 23548055

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

Todd K Hyster1, Kyle E Ruhl, Tomislav Rovis.   

Abstract

The coupling of O-pivaloyl benzhydroxamic acids with donor/acceptor diazo compounds provides isoindolones in high yield. The reaction tolerates a broad range of benzhydroxamic acids and diazo compounds, including substituted 2,2,2-trifluorodiazoethanes. Mechanistic experiments suggested that C-H activation is turnover-limiting and irreversible and that insertion of the diazo compound favors electron-deficient substrates.

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Year:  2013        PMID： 23548055      PMCID： PMC3658175          DOI： 10.1021/ja402274g

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


  38 in total

1.  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

2.  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

3.  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

4.  Asymmetric synthesis of 3-substituted isoindolinones: application to the total synthesis of (+)-lennoxamine.

Authors:  Daniel L Comins; Stefan Schilling; Yanchen Zhang
Journal:  Org Lett       Date:  2005-01-06       Impact factor: 6.005

5.  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

6.  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

7.  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

8.  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

9.  Isoindolinone enantiomers having affinity for the dopamine D4 receptor.

Authors:  T R Belliotti; W A Brink; S R Kesten; J R Rubin; D J Wustrow; K T Zoski; S Z Whetzel; A E Corbin; T A Pugsley; T G Heffner; L D Wise
Journal:  Bioorg Med Chem Lett       Date:  1998-06-16       Impact factor: 2.823

10.  Chiral cyclopentadienyl ligands as stereocontrolling element in asymmetric C-H functionalization.

Authors:  Baihua Ye; Nicolai Cramer
Journal:  Science       Date:  2012-10-26       Impact factor: 47.728
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  25 in total

1.  Rh2(R-TPCP)4-catalyzed enantioselective [3+2]-cycloaddition between nitrones and vinyldiazoacetates.

Authors:  Changming Qin; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2013-09-20       Impact factor: 15.419

2.  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

3.  Three-Component Coupling of Aldehydes, 2-Aminopyridines, and Diazo Esters via Rhodium(III)-Catalyzed Imidoyl C-H Activation: Synthesis of Pyrido[1,2- a]pyrimidin-4-ones.

Authors:  Gia L Hoang; Adam J Zoll; Jonathan A Ellman
Journal:  Org Lett       Date:  2019-03-21       Impact factor: 6.005

Review 4.  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

Review 5.  A Simple and Versatile Amide Directing Group for C-H Functionalizations.

Authors:  Ru-Yi Zhu; Marcus E Farmer; Yan-Qiao Chen; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-01       Impact factor: 15.336

6.  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

7.  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 8.  Cycloaddition reactions of enoldiazo compounds.

Authors:  Qing-Qing Cheng; Yongming Deng; Marianne Lankelma; Michael P Doyle
Journal:  Chem Soc Rev       Date:  2017-08-29       Impact factor: 54.564

9.  Rhodium-Catalyzed Enantioselective Cycloisomerization to Cyclohexenes Bearing Quaternary Carbon Centers.

Authors:  Jung-Woo Park; Zhiwei Chen; Vy M Dong
Journal:  J Am Chem Soc       Date:  2016-03-08       Impact factor: 15.419

10.  Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C-H Activation.

Authors:  Fedor Romanov-Michailidis; Kassandra F Sedillo; Jamie M Neely; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2015-07-08       Impact factor: 15.419
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