Literature DB >> 19170153

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

Chris E Houlden1, Marc Hutchby, Chris D Bailey, J Gair Ford, Simon N G Tyler, Michel R Gagné, Guy C Lloyd-Jones, Kevin I Booker-Milburn.   

Abstract

Pd and CO--ureally got me! The title reaction proceeds efficiently at 18 degrees C under CO (1 atm) with 5 % [Pd(OTs)(2)(MeCN)(2)] as precatalyst. Depending on the solvents used, either anthranilates or cyclic imides can be obtained in high yields (see picture, BQ = benzoquinone, Ts = 4-toluenesulfonyl).

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Year:  2009        PMID： 19170153      PMCID： PMC2661427          DOI： 10.1002/anie.200805842

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  15 in total

1.  Highly selective C-H functionalization/halogenation of acetanilide.

Authors:  Xiaobing Wan; Zhongxun Ma; Bijie Li; Keya Zhang; Shaokui Cao; Shiwei Zhang; Zhangjie Shi
Journal:  J Am Chem Soc       Date:  2006-06-14       Impact factor: 15.419

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

Review 3.  The potential of palladacycles: more than just precatalysts.

Authors:  Jairton Dupont; Crestina S Consorti; John Spencer
Journal:  Chem Rev       Date:  2005-06       Impact factor: 60.622

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.  Multiple C-H activations to construct biologically active molecules in a process completely free of organohalogen and organometallic components.

Authors:  Bi-Jie Li; Shi-Liang Tian; Zhao Fang; Zhang-Jie Shi
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Ortho arylation of acetanilides via Pd(II)-catalyzed C-H functionalization.

Authors:  Shangdong Yang; Bijie Li; Xiaobing Wan; Zhangjie Shi
Journal:  J Am Chem Soc       Date:  2007-04-25       Impact factor: 15.419

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

Authors:  Gordon Brasche; Jorge García-Fortanet; Stephen L Buchwald
Journal:  Org Lett       Date:  2008-05-09       Impact factor: 6.005

8.  Alcoholysis of Urea Catalyzed by Palladium(II) Complexes.

Authors:  Natalia V. Kaminskaia; Nenad M. Kostic
Journal:  Inorg Chem       Date:  1998-08-24       Impact factor: 5.165

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

Authors:  Chris E Houlden; Chris D Bailey; J Gair Ford; Michel R Gagné; Guy C Lloyd-Jones; Kevin I Booker-Milburn
Journal:  J Am Chem Soc       Date:  2008-07-10       Impact factor: 15.419

10.  Microwave-assisted efficient and convenient synthesis of 2,4(1H,3H)-quinazolinediones and 2-thioxoquinazolines.

Authors:  Zhaoguang Li; He Huang; Hongbin Sun; Hualiang Jiang; Hong Liu
Journal:  J Comb Chem       Date:  2008-04-18
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  12 in total

1.  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

2.  Aminoquinoline-directed, cobalt-catalyzed carbonylation of sulfonamide sp2 C-H bonds.

Authors:  Tung Thanh Nguyen; Liene Grigorjeva; Olafs Daugulis
Journal:  Chem Commun (Camb)       Date:  2017-05-04       Impact factor: 6.222

3.  Storable N-phenylcarbamate palladacycles for rapid functionalization of an alkyne-encoded protein.

Authors:  Gang Cheng; Reyna K V Lim; Carlo P Ramil; Qing Lin
Journal:  Chem Commun (Camb)       Date:  2014-10-11       Impact factor: 6.222

4.  Cationic Pd(II)-catalyzed Fujiwara-Moritani reactions at room temperature in water.

Authors:  Takashi Nishikata; Bruce H Lipshutz
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

5.  General method for the synthesis of salicylic acids from phenols through palladium-catalyzed silanol-directed C-H carboxylation.

Authors:  Yang Wang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-19       Impact factor: 15.336

6.  Pd(II)-catalyzed carbonylation of C(sp3)-H bonds: a new entry to 1,4-dicarbonyl compounds.

Authors:  Eun Jeong Yoo; Masayuki Wasa; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-11-17       Impact factor: 15.419

7.  Cationic palladium(II) catalysis: C-H activation/Suzuki-Miyaura couplings at room temperature.

Authors:  Takashi Nishikata; Alexander R Abela; Shenlin Huang; Bruce H Lipshutz
Journal:  J Am Chem Soc       Date:  2010-04-14       Impact factor: 15.419

8.  Hindered ureas as masked isocyanates: facile carbamoylation of nucleophiles under neutral conditions.

Authors:  Marc Hutchby; Chris E Houlden; 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

Review 9.  Palladium-catalyzed ligand-directed C-H functionalization reactions.

Authors:  Thomas W Lyons; Melanie S Sanford
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

10.  Synthesis of conformationally restricted glutamate and glutamine derivatives from carbonylation of orthopalladated phenylglycine derivatives.

Authors:  Esteban P Urriolabeitia; Eduardo Laga; Carlos Cativiela
Journal:  Beilstein J Org Chem       Date:  2012-09-18       Impact factor: 2.883
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