Literature DB >> 27540274

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

Tyler A Davis1, Chuanqi Wang1, Tomislav Rovis1.   

Abstract

Carboxylic acids effectively direct C-H activation for Rhodium(III)-catalyzed intramolecular Heck-type reactions. A catalytic amount of Cu(OAc)2 is used as the external oxidant with oxygen likely acting as the terminal oxidant. Additionally, a novel electron-deficient RhIII catalyst was found to be more effective that [RhCp*Cl2]2 with some substrates. A wide variety of complex dihydrobenzofurans, dihydrobenzopyrans, and other bicycles that can be easily further functionalized are now accessible through relatively mild reaction conditions.

Entities:  

Keywords:  C-H activation; Heck reaction; Rhodium (III) catalysis; cyclization; dihydrobenzofurans

Year:  2015        PMID: 27540274      PMCID: PMC4986923          DOI: 10.1055/s-0034-1381006

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


  25 in total

1.  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

2.  Pyridine synthesis from oximes and alkynes via rhodium(III) catalysis: Cp* and Cp(t) provide complementary selectivity.

Authors:  Todd K Hyster; Tomislav Rovis
Journal:  Chem Commun (Camb)       Date:  2011-10-10       Impact factor: 6.222

3.  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

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

Authors:  Todd K Hyster; Tomislav Rovis
Journal:  Synlett       Date:  2013       Impact factor: 2.454

5.  Chiral Cp-rhodium(III)-catalyzed asymmetric hydroarylations of 1,1-disubstituted alkenes.

Authors:  Baihua Ye; Pavel A Donets; Nicolai Cramer
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-06       Impact factor: 15.336

6.  Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes via regioselective C-H bond cleavage.

Authors:  Kenji Ueura; Tetsuya Satoh; Masahiro Miura
Journal:  J Org Chem       Date:  2007-06-06       Impact factor: 4.354

7.  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

8.  An efficient waste-free oxidative coupling via regioselective C-H bond cleavage: Rh/Cu-catalyzed reaction of benzoic acids with alkynes and acrylates under air.

Authors:  Kenji Ueura; Tetsuya Satoh; Masahiro Miura
Journal:  Org Lett       Date:  2007-03-09       Impact factor: 6.005

9.  Rh(III)-catalyzed decarboxylative coupling of acrylic acids with unsaturated oxime esters: carboxylic acids serve as traceless activators.

Authors:  Jamie M Neely; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2014-02-10       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

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  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.  RhodiumIII-catalyzed remote difunctionalization of arenes assisted by a relay directing group.

Authors:  Lincong Sun; Yuyao Zhao; Bingxian Liu; Junbiao Chang; Xingwei Li
Journal:  Chem Sci       Date:  2022-05-30       Impact factor: 9.969

4.  Intramolecular radical cyclization approach to access highly substituted indolines and 2,3-dihydrobenzofurans under visible-light.

Authors:  Clarice A D Caiuby; Akbar Ali; Vinicius T Santana; Francisco W de S Lucas; Marilia S Santos; Arlene G Corrêa; Otaciro R Nascimento; Hao Jiang; Márcio W Paixão
Journal:  RSC Adv       Date:  2018-04-05       Impact factor: 4.036

5.  Rh(III)-Catalyzed Aryl and Alkenyl C-H Bond Addition to Diverse Nitroalkenes.

Authors:  Tyler J Potter; David N Kamber; Brandon Q Mercado; Jonathan A Ellman
Journal:  ACS Catal       Date:  2016-12-02       Impact factor: 13.084

Review 6.  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

7.  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

8.  A β-Carbon elimination strategy for convenient in situ access to cyclopentadienyl metal complexes.

Authors:  G Smits; B Audic; M D Wodrich; C Corminboeuf; N Cramer
Journal:  Chem Sci       Date:  2017-08-24       Impact factor: 9.825

9.  Overcoming naphthoquinone deactivation: rhodium-catalyzed C-5 selective C-H iodination as a gateway to functionalized derivatives.

Authors:  Guilherme A M Jardim; Eufrânio N da Silva Júnior; John F Bower
Journal:  Chem Sci       Date:  2016-03-02       Impact factor: 9.825

10.  Rh(iii)-catalyzed tandem annulative redox-neutral arylation/amidation of aromatic tethered alkenes.

Authors:  Chao Chen; Chen Shi; Yaxi Yang; Bing Zhou
Journal:  Chem Sci       Date:  2020-10-16       Impact factor: 9.825

  10 in total

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