Literature DB >> 19580277

Pd(0)/PR3-catalyzed intermolecular arylation of sp3 C-H bonds.

Masayuki Wasa1, Keary M Engle, Jin-Quan Yu.   

Abstract

Pd(0)-catalyzed intermolecular arylation of sp(3) C-H bonds has been achieved using PR(3)/ArI. This protocol can be used to arylate a variety of aliphatic carboxylic acid derivatives, including a number of bioactive drug molecules. The use of fluorinated aryl iodides also allows for the introduction of fluorine into a molecule of interest.

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Year:  2009        PMID： 19580277      PMCID： PMC2727875          DOI： 10.1021/ja903573p

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


  17 in total

1.  The palladium-catalyzed C-H activation of benzylic gem-dialkyl groups.

Authors:  Olivier Baudoin; Audrey Herrbach; Françoise Guéritte
Journal:  Angew Chem Int Ed Engl       Date:  2003-12-01       Impact factor: 15.336

2.  Consecutive vinylic to aryl to allylic palladium migration and multiple C-H activation processes.

Authors:  Jian Zhao; Marino Campo; Richard C Larock
Journal:  Angew Chem Int Ed Engl       Date:  2005-03-11       Impact factor: 15.336

3.  Palladium-catalyzed benzene arylation: incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design.

Authors:  Marc Lafrance; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

4.  Synthesis of 1,2- and 1,3-dicarboxylic acids via Pd(II)-catalyzed carboxylation of aryl and vinyl C-H bonds.

Authors:  Ramesh Giri; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2008-10-04       Impact factor: 15.419

5.  Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Authors:  Timothy E Barder; Shawn D Walker; Joseph R Martinelli; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

6.  High-yielding palladium-catalyzed intramolecular alkane arylation: reaction development and mechanistic studies.

Authors:  Marc Lafrance; Serge I Gorelsky; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2007-11-07       Impact factor: 15.419

7.  Pd(II)-catalyzed cross-coupling of sp3 C-H Bonds with sp2 and sp3 boronic acids using air as the oxidant.

Authors:  Dong-Hui Wang; Masayuki Wasa; Ramesh Giri; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2008-05-14       Impact factor: 15.419

8.  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

9.  Palladium-catalyzed sp(3) CH activation of simple alkyl groups: direct preparation of indoline derivatives from N-alkyl-2-bromoanilines.

Authors:  Toshiaki Watanabe; Shinya Oishi; Nobutaka Fujii; Hiroaki Ohno
Journal:  Org Lett       Date:  2008-04-08       Impact factor: 6.005

10.  Palladium-catalyzed arylation and heteroarylation of indolizines.

Authors:  Choul-Hong Park; Victoria Ryabova; Ilya V Seregin; Anna W Sromek; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2004-04-01       Impact factor: 6.005
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  57 in total

1.  Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions.

Authors:  Keary M Engle; Tian-Sheng Mei; Masayuki Wasa; Jin-Quan Yu
Journal:  Acc Chem Res       Date:  2011-12-14       Impact factor: 22.384

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.  Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors:  Dmitry Shabashov; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

4.  Total synthesis and structural revision of the piperarborenines via sequential cyclobutane C-H arylation.

Authors:  Will R Gutekunst; Phil S Baran
Journal:  J Am Chem Soc       Date:  2011-11-08       Impact factor: 15.419

5.  γ,δ,ε-C(sp(3))-H Functionalization through Directed Radical H-Abstraction.

Authors:  Tao Liu; Tian-Sheng Mei; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-04-30       Impact factor: 15.419

6.  Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups.

Authors:  Gang Li; Li Wan; Guofu Zhang; Dasheng Leow; Jillian Spangler; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-03-24       Impact factor: 15.419

7.  Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.

Authors:  Enrico T Nadres; Gerson Ivan Franco Santos; Dmitry Shabashov; Olafs Daugulis
Journal:  J Org Chem       Date:  2013-09-19       Impact factor: 4.354

8.  Pd0/PR3-catalyzed arylation of nicotinic and isonicotinic acid derivatives.

Authors:  Masayuki Wasa; Brady T Worrell; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2010-02-08       Impact factor: 15.336

9.  Photoredox activation for the direct β-arylation of ketones and aldehydes.

Authors:  Michael T Pirnot; Danica A Rankic; David B C Martin; David W C MacMillan
Journal:  Science       Date:  2013-03-29       Impact factor: 47.728

10.  Ligand-Promoted Borylation of C(sp(3))-H Bonds with Palladium(II) Catalysts.

Authors:  Jian He; Heng Jiang; Ryosuke Takise; Ru-Yi Zhu; Gang Chen; Hui-Xiong Dai; T G Murali Dhar; Jun Shi; Hao Zhang; Peter T W Cheng; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-27       Impact factor: 15.336
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