Literature DB >> 22377832

C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation.

Guoyong Song1, Fen Wang, Xingwei Li.   

Abstract

Rhodium(III)-catalyzed direct functionalization of C-H bonds under oxidative conditions leading to C-C, C-N, and C-O bond formation is reviewed. Various arene substrates bearing nitrogen and oxygen directing groups are covered in their coupling with unsaturated partners such as alkenes and alkynes. The facile construction of C-E (E = C, N, S, or O) bonds makes Rh(III) catalysis an attractive step-economic approach to value-added molecules from readily available starting materials. Comparisons and contrasts between rhodium(III) and palladium(II)-catalyzed oxidative coupling are made. The remarkable diversity of structures accessible is demonstrated with various recent examples, with a proposed mechanism for each transformation being briefly summarized (critical review, 138 references). This journal is © The Royal Society of Chemistry 2012

Entities:  

Year:  2012        PMID: 22377832     DOI: 10.1039/c2cs15281a

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  101 in total

1.  Rh(III)-Catalyzed C-H Bond Addition/Amine-Mediated Cyclization of Bis-Michael Acceptors.

Authors:  Tyler J Potter; Jonathan A Ellman
Journal:  Org Lett       Date:  2016-07-20       Impact factor: 6.005

2.  Scalable and chromatography-free synthesis of 2-(2-formylalkyl)arenecarboxylic acid derivatives through the supramolecularly controlled hydroformylation of vinylarene-2-carboxylic acids.

Authors:  Paweł Dydio; Joost N H Reek
Journal:  Nat Protoc       Date:  2014-04-24       Impact factor: 13.491

3.  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

4.  Facile Rh(III)-Catalyzed Synthesis of Fluorinated Pyridines.

Authors:  Shuming Chen; Robert G Bergman; Jonathan A Ellman
Journal:  Org Lett       Date:  2015-05-20       Impact factor: 6.005

5.  Stereodivergent Rhodium(III)-Catalyzed cis-Cyclopropanation Enabled by Multivariate Optimization.

Authors:  Tiffany Piou; Fedor Romanov-Michailidis; Melissa A Ashley; Maria Romanova-Michaelides; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2018-07-23       Impact factor: 15.419

6.  Rhodium(III)-catalyzed intramolecular hydroarylation, amidoarylation, and Heck-type reaction: three distinct pathways determined by an amide directing group.

Authors:  Tyler A Davis; Todd K Hyster; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-08       Impact factor: 15.336

7.  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

8.  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

9.  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

10.  Dehydrogenative alkenylation of uracils via palladium-catalyzed regioselective C-H activation.

Authors:  Yi-Yun Yu; Gunda I Georg
Journal:  Chem Commun (Camb)       Date:  2013-03-25       Impact factor: 6.222

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