Literature DB >> 18465866

Twofold C-H functionalization: palladium-catalyzed ortho arylation of anilides.

Gordon Brasche1, Jorge García-Fortanet, Stephen L Buchwald.   

Abstract

The ortho arylation of anilides to form biphenyls via a twofold C-H functionalization/C-C bond-forming process is described. The oxidative coupling takes place in the presence of 5-10 mol % of Pd(OAc)2, 10-20 mol % of DMSO, and 4-11 equiv of the aryl substrate in TFA under an oxygen atmosphere. No metal-containing cocatalyst is required.

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Year:  2008        PMID： 18465866      PMCID： PMC2489205          DOI： 10.1021/ol800619c

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  29 in total

1.  Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: reactions and mechanistic aspects.

Authors:  Vincent Ritleng; Claude Sirlin; Michel Pfeffer
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

2.  Sequential hydrocarbon functionalization: allylic C-H oxidation/vinylic C-H arylation.

Authors:  Jared H Delcamp; M Christina White
Journal:  J Am Chem Soc       Date:  2006-11-29       Impact factor: 15.419

3.  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

Review 4.  Sigma-chelation-directed C-H functionalizations using Pd(II) and Cu(II) catalysts: regioselectivity, stereoselectivity and catalytic turnover.

Authors:  Jin-Quan Yu; Ramesh Giri; Xiao Chen
Journal:  Org Biomol Chem       Date:  2006-11-21       Impact factor: 3.876

5.  C-H bond functionalization in complex organic synthesis.

Authors:  Kamil Godula; Dalibor Sames
Journal:  Science       Date:  2006-04-07       Impact factor: 47.728

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.  C-H Bond Functionalizations with Palladium(II): Intramolecular Oxidative Annulations of Arenes.

Authors:  Eric M Ferreira; Haiming Zhang; Brian M Stoltz
Journal:  Tetrahedron       Date:  2008-06-23       Impact factor: 2.457

8.  Elements of regiocontrol in palladium-catalyzed oxidative arene cross-coupling.

Authors:  David R Stuart; Elisia Villemure; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2007-09-19       Impact factor: 15.419

Review 9.  Palladium oxidase catalysis: selective oxidation of organic chemicals by direct dioxygen-coupled turnover.

Authors:  Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2004-06-28       Impact factor: 15.336

10.  Two methods for direct ortho-arylation of benzoic acids.

Authors:  Hendrich A Chiong; Quynh-Nhu Pham; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2007-07-25       Impact factor: 15.419
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  30 in total

1.  Pd(II)-catalyzed para-selective C-H arylation of monosubstituted arenes.

Authors:  Xisheng Wang; Dasheng Leow; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2011-08-16       Impact factor: 15.419

2.  A general method for copper-catalyzed arene cross-dimerization.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2011-08-08       Impact factor: 15.419

3.  Regiocontrolled aerobic oxidative coupling of indoles and benzene using Pd catalysts with 4,5-diazafluorene ligands.

Authors:  Alison N Campbell; Eric B Meyer; Shannon S Stahl
Journal:  Chem Commun (Camb)       Date:  2011-08-22       Impact factor: 6.222

4.  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

5.  Characterization of DMSO coordination to palladium(II) in solution and insights into the aerobic oxidation catalyst, Pd(DMSO)2(TFA)2.

Authors:  Tianning Diao; Paul White; Ilia Guzei; Shannon S Stahl
Journal:  Inorg Chem       Date:  2012-10-23       Impact factor: 5.165

6.  Palladium-catalyzed C-H functionalization using guanidine as a directing group: ortho arylation and olefination of arylguanidines.

Authors:  Jiaan Shao; Wenteng Chen; Marc A Giulianotti; Richard A Houghten; Yongping Yu
Journal:  Org Lett       Date:  2012-10-24       Impact factor: 6.005

7.  A general method for copper-catalyzed arylation of arene C-H bonds.

Authors:  Hien-Quang Do; Rana M Kashif Khan; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2008-10-15       Impact factor: 15.419

8.  Synthetic and mechanistic studies of Pd-catalyzed C-H arylation with diaryliodonium salts: evidence for a bimetallic high oxidation state Pd intermediate.

Authors:  Nicholas R Deprez; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2009-08-12       Impact factor: 15.419

9.  The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective ortho-Acyloxylation and ortho-Halogenation Reactions of Arenes.

Authors:  Chunhui Huang; Natalia Chernyak; Alexander S Dudnik; Vladimir Gevorgyan
Journal:  Adv Synth Catal       Date:  2011-05-01       Impact factor: 5.837

10.  Mild aromatic palladium-catalyzed protodecarboxylation: kinetic assessment of the decarboxylative palladation and the protodepalladation steps.

Authors:  Joshua S Dickstein; John M Curto; Osvaldo Gutierrez; Carol A Mulrooney; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2013-04-29       Impact factor: 4.354
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