Literature DB >> 25346576

Rhodium(III)-Catalyzed C-H Activation Mediated Synthesis of Isoquinolones from Amides and Cyclopropenes.

Todd K Hyster1, Tomislav Rovis1.   

Abstract

We have developed a synthesis of 4-substituted isoquinolones from the Rh(III)-catalyzed, C-H activation mediated, coupling of O-pivaloyl benzhydroxamic acids and 3,3-disubstituted cyclopropenes. Experiments suggest the formation of a [4.1.0] bicyclic-system, which can open under acidic conditions to generate the desired isoquinolone.

Entities:  

Keywords:  C–H activation; cyclopropene; donor-acceptor cyclopropane; heterocycles; isoquinolone

Year:  2013        PMID： 25346576      PMCID： PMC4206942          DOI： 10.1055/s-0033-1339510

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  18 in total

1.  Donor-acceptor-substituted cyclopropane derivatives and their application in organic synthesis.

Authors:  Hans-Ulrich Reissig; Reinhold Zimmer
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

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.  Catalytic [3+2] annulation of aminocyclopropanes for the enantiospecific synthesis of cyclopentylamines.

Authors:  Florian de Nanteuil; Jérôme Waser
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-26       Impact factor: 15.336

4.  Mild rhodium(III)-catalyzed C-H activation and intermolecular annulation with allenes.

Authors:  Honggen Wang; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-18       Impact factor: 15.336

5.  Catalytic selective cyclizations of aminocyclopropanes: formal synthesis of aspidospermidine and total synthesis of goniomitine.

Authors:  Filippo De Simone; Jürg Gertsch; Jérôme Waser
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-02       Impact factor: 15.336

6.  Transition metal chemistry of cyclopropenes and cyclopropanes.

Authors:  Michael Rubin; Marina Rubina; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2007-07       Impact factor: 60.622

Review 7.  Heterocycles from cyclopropanes: applications in natural product synthesis.

Authors:  Cheryl A Carson; Michael A Kerr
Journal:  Chem Soc Rev       Date:  2009-07-10       Impact factor: 54.564

8.  Catalytic enantiospecific [3+2] annulation of aminocyclopropanes with ketones.

Authors:  Fides Benfatti; Florian de Nanteuil; Jérôme Waser
Journal:  Chemistry       Date:  2012-03-15       Impact factor: 5.236

9.  Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones.

Authors:  Marc Presset; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  Org Lett       Date:  2013-03-15       Impact factor: 6.005

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
View more
  10 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

Review 2.  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

3.  Regiodivergent Iridium(III)-Catalyzed Diamination of Alkenyl Amides with Secondary Amines: Complementary Access to γ- or δ-Lactams.

Authors:  John H Conway; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2017-12-26       Impact factor: 15.419

4.  Rhodium(III)-Catalyzed Allylic C(sp(3))-H Activation of Alkenyl Sulfonamides: Unexpected Formation of Azabicycles.

Authors:  Alexis Archambeau; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-11       Impact factor: 15.336

5.  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

6.  Rhodium(III)-Catalyzed C-H Activation: An Oxidative Intramolecular Heck-Type Reaction Directed by a Carboxylic Acid.

Authors:  Tyler A Davis; Chuanqi Wang; Tomislav Rovis
Journal:  Synlett       Date:  2015-06-15       Impact factor: 2.454

7.  RhIII-Catalyzed Synthesis of Isoquinolones and 2-Pyridones via Annulation of N-Methoxyamides and Nitroalkenes.

Authors:  Tyler J Potter; Yuantao Li; Michael D Ward; Jonathan A Ellman
Journal:  European J Org Chem       Date:  2018-06-11

8.  Heptamethylindenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(iii)-catalyzed C-H activation.

Authors:  Natthawat Semakul; Kelvin E Jackson; Robert S Paton; Tomislav Rovis
Journal:  Chem Sci       Date:  2016-09-23       Impact factor: 9.825

9.  Rh(III)-catalyzed cyclopropanation initiated by C-H activation: ligand development enables a diastereoselective [2 + 1] annulation of N-enoxyphthalimides and alkenes.

Authors:  Tiffany Piou; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2014-08-05       Impact factor: 15.419

10.  Ligand Design for Rh(III)-Catalyzed C-H Activation: An Unsymmetrical Cyclopentadienyl Enables a Regioselective Synthesis of Dihydroisoquinolones.

Authors:  Todd K Hyster; Derek M Dalton; Tomislav Rovis
Journal:  Chem Sci       Date:  2015-01-01       Impact factor: 9.825
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.