Literature DB >> 18613664

Distinct reactivity of Pd(OTs)2: the intermolecular Pd(II)-catalyzed 1,2-carboamination of dienes.

Chris E Houlden1, Chris D Bailey, J Gair Ford, Michel R Gagné, Guy C Lloyd-Jones, Kevin I Booker-Milburn.   

Abstract

A Pd-catalyzed intermolecular 1,2-carboamination route to indolines from N-aryl ureas and 1,3-dienes that proceeds under mild conditions in relatively nonacidic media, is presented. The in situ generation, or preformation, of a palladium tosylate emerges as a key parameter in gaining the requisite reactivity for the C-H insertion/carbopalladation/nucleophilic displacement process.

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Year:  2008        PMID： 18613664      PMCID： PMC2674574          DOI： 10.1021/ja803397y

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


  22 in total

1.  1,2-Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis.

Authors:  David J. Ager; Indra Prakash; David R. Schaad
Journal:  Chem Rev       Date:  1996-03-28       Impact factor: 60.622

2.  Anilide ortho-arylation by using C-H activation methodology.

Authors:  Olafs Daugulis; Vladimir G Zaitsev
Journal:  Angew Chem Int Ed Engl       Date:  2005-06-27       Impact factor: 15.336

3.  Room temperature palladium-catalyzed 2-arylation of indoles.

Authors:  Nicholas R Deprez; Dipannita Kalyani; Andrew Krause; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2006-04-19       Impact factor: 15.419

Review 4.  Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

Authors:  Dino Alberico; Mark E Scott; Mark Lautens
Journal:  Chem Rev       Date:  2007-01       Impact factor: 60.622

5.  Copper(II) acetate promoted intramolecular diamination of unactivated olefins.

Authors:  Thomas P Zabawa; Dhanalakshmi Kasi; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

6.  Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature.

Authors:  Maarten D K Boele; Gino P F van Strijdonck; André H M de Vries; Paul C J Kamer; Johannes G de Vries; Piet W N M van Leeuwen
Journal:  J Am Chem Soc       Date:  2002-02-27       Impact factor: 15.419

7.  Pd(II)-catalyzed intermolecular 1,2-diamination of conjugated dienes.

Authors:  Grégory L J Bar; Guy C Lloyd-Jones; Kevin I Booker-Milburn
Journal:  J Am Chem Soc       Date:  2005-05-25       Impact factor: 15.419

8.  Palladium(II)-catalyzed intramolecular diamination of unfunctionalized alkenes.

Authors:  Jan Streuff; Claas H Hövelmann; Martin Nieger; Kilian Muñiz
Journal:  J Am Chem Soc       Date:  2005-10-26       Impact factor: 15.419

Review 9.  Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry.

Authors:  S R S Saibabu Kotti; Cody Timmons; Guigen Li
Journal:  Chem Biol Drug Des       Date:  2006-02       Impact factor: 2.817

10.  Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: regioselective and switchable C-H alkenylation and annulation of pyrroles.

Authors:  Elizabeth M Beck; Neil P Grimster; Richard Hatley; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419
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  24 in total

1.  Ligand-Accelerated ortho-C-H Olefination of Phenylacetic Acids.

Authors:  Keary M Engle; Navid Dastbaravardeh; Peter S Thuy-Boun; Dong-Hui Wang; Aaron C Sather; Jin-Quan Yu
Journal:  Organic Synth       Date:  2015-03-12

2.  Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

Authors:  Tian-Sheng Mei; Lei Kou; Sandy Ma; Keary M Engle; Jin-Quan Yu
Journal:  Synthesis (Stuttg)       Date:  2012-05-25       Impact factor: 3.157

3.  Cobalt-Catalyzed Coupling of Benzoic Acid C-H Bonds with Alkynes, Styrenes, and 1,3-Dienes.

Authors:  Tung Thanh Nguyen; Liene Grigorjeva; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-10       Impact factor: 15.336

4.  Diastereo- and enantioselective copper-catalyzed intramolecular carboamination of alkenes for the synthesis of hexahydro-1H-benz[f]indoles.

Authors:  Lei Miao; Imranul Haque; Maria R Manzoni; Weng Siong Tham; Sherry R Chemler
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

5.  Pd(II)-catalyzed hydroxyl-directed C-H olefination enabled by monoprotected amino acid ligands.

Authors:  Yi Lu; Dong-Hui Wang; Keary M Engle; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-04-28       Impact factor: 15.419

6.  Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and Beyond.

Authors:  Kelvin Pak Shing Cheung; Daria Kurandina; Tetsuji Yata; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2020-05-19       Impact factor: 15.419

7.  Palladium-catalyzed aerobic oxidative dehydrogenation of cyclohexenes to substituted arene derivatives.

Authors:  Andrei V Iosub; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2015-03-09       Impact factor: 15.419

8.  Room-temperature palladium-catalyzed C-H activation: ortho-carbonylation of aniline derivatives.

Authors:  Chris E Houlden; Marc Hutchby; Chris D Bailey; J Gair Ford; Simon N G Tyler; Michel R Gagné; Guy C Lloyd-Jones; Kevin I Booker-Milburn
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Nickel-Catalyzed Dearomative trans-1,2-Carboamination.

Authors:  Lucas W Hernandez; Ulrich Klöckner; Jola Pospech; Lilian Hauss; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-03-23       Impact factor: 15.419

10.  Pd(II)-catalyzed olefination of electron-deficient arenes using 2,6-dialkylpyridine ligands.

Authors:  Yang-Hui Zhang; Bing-Feng Shi; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2009-04-15       Impact factor: 15.419
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