Literature DB >> 12440873

Intermolecular coupling of isomerizable alkenes to heterocycles via rhodium-catalyzed C-H bond activation.

Kian L Tan1, Robert G Bergman, Jonathan A Ellman.   

Abstract

This reports first intermolecular coupling of unactivated alkenes, including isomerizable alkenes, to a range of heterocycles using a Rh(I) catalyst. A variety of functional groups were incorporated, including esters, nitriles, and acetals. The intermolecular coupling became possible after it was discovered that weak acids dramatically increase the rate of both the inter- and intramolecular reactions.

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Year:  2002        PMID: 12440873     DOI: 10.1021/ja0281129

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


  17 in total

Review 1.  Direct transition metal-catalyzed functionalization of heteroaromatic compounds.

Authors:  Ilya V Seregin; Vladimir Gevorgyan
Journal:  Chem Soc Rev       Date:  2007-03-05       Impact factor: 54.564

2.  Rh(I)-catalyzed alkylation of quinolines and pyridines via C-H bond activation.

Authors:  Jared C Lewis; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2007-04-06       Impact factor: 15.419

3.  C2-Selective Branched Alkylation of Benzimidazoles by Rhodium(I)-Catalyzed C-H Activation.

Authors:  Gaël Tran; Danielle Confair; Kevin D Hesp; Vincent Mascitti; Jonathan A Ellman
Journal:  J Org Chem       Date:  2017-08-22       Impact factor: 4.354

4.  Reactions of Indene and Indoles with Platinum Methyl Cations: Indene C-H Activation, Indole π vs. Nitrogen Lone-Pair Coordination.

Authors:  Travis J Williams; Jay A Labinger; John E Bercaw
Journal:  Organometallics       Date:  2007       Impact factor: 3.876

5.  Synthesis of a Benzodiazepine-derived Rhodium NHC Complex by C-H Bond Activation.

Authors:  Michael W Gribble; Jonathan A Ellman; Robert G Bergman
Journal:  Organometallics       Date:  2008-05-26       Impact factor: 3.876

6.  Rhodium catalyzed enantioselective cyclization of substituted imidazoles via C-H bond activation.

Authors:  Andy S Tsai; Rebecca M Wilson; Hitoshi Harada; Robert G Bergman; Jonathan A Ellman
Journal:  Chem Commun (Camb)       Date:  2009-06-02       Impact factor: 6.222

Review 7.  Direct functionalization of nitrogen heterocycles via Rh-catalyzed C-H bond activation.

Authors:  Jared C Lewis; Robert G Bergman; Jonathan A Ellman
Journal:  Acc Chem Res       Date:  2008-07-11       Impact factor: 22.384

Review 8.  Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.

Authors:  Denise A Colby; Robert G Bergman; Jonathan A Ellman
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

9.  Computational prediction of the regio- and diastereoselectivity in a rhodium-catalyzed hydroformylation/cyclization domino process.

Authors:  Giuliano Alagona; Caterina Ghio; Silvia Rocchiccioli
Journal:  J Mol Model       Date:  2007-05-22       Impact factor: 1.810

10.  Experimental and computational studies on the mechanism of N-heterocycle C-H activation by Rh(I).

Authors:  Sean H Wiedemann; Jared C Lewis; Jonathan A Ellman; Robert G Bergman
Journal:  J Am Chem Soc       Date:  2006-02-22       Impact factor: 15.419

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