Literature DB >> 18855360

Rh(I)-catalyzed direct arylation of pyridines and quinolines.

Ashley M Berman1, Jared C Lewis, Robert G Bergman, Jonathan A Ellman.   

Abstract

A Rh(I)-catalyzed direct arylation of pyridine and quinoline heterocycles has been developed. The method provides rapid entry into an important class of substituted heterocycles employing inexpensive and readily available starting materials.

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Year:  2008        PMID： 18855360      PMCID： PMC2647742          DOI： 10.1021/ja8059396

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


  13 in total

Review 1.  Analysis of the reactions used for the preparation of drug candidate molecules.

Authors:  John S Carey; David Laffan; Colin Thomson; Mike T Williams
Journal:  Org Biomol Chem       Date:  2006-05-03       Impact factor: 3.876

Review 2.  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

3.  A strategy for C-H activation of pyridines: direct C-2 selective alkenylation of pyridines by nickel/Lewis acid catalysis.

Authors:  Yoshiaki Nakao; Kyalo Stephen Kanyiva; Tamejiro Hiyama
Journal:  J Am Chem Soc       Date:  2008-02-05       Impact factor: 15.419

4.  Understanding the formation of N-H tautomers from alpha-substituted pyridines: tautomerization of 2-ethylpyridine promoted by osmium.

Authors:  María L Buil; Miguel A Esteruelas; Karin Garcés; Montserrat Oliván; Enrique Oñate
Journal:  J Am Chem Soc       Date:  2007-08-16       Impact factor: 15.419

5.  Rhodium-catalyzed regioselective C-H functionalization via decarbonylation of acid chlorides and C-H bond activation under phosphine-free conditions.

Authors:  Xiaodan Zhao; Zhengkun Yu
Journal:  J Am Chem Soc       Date:  2008-06-10       Impact factor: 15.419

6.  A solution to the 2-pyridyl organometallic cross-coupling problem: regioselective catalytic direct arylation of pyridine N-oxides.

Authors:  Louis-Charles Campeau; Sophie Rousseaux; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2005-12-28       Impact factor: 15.419

7.  Palladium-catalyzed cross-coupling reactions of diazine N-oxides with aryl chlorides, bromides, and iodides.

Authors:  Jean-Philippe Leclerc; Keith Fagnou
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-27       Impact factor: 15.336

8.  Palladium-catalyzed C-H functionalization of pyridine N-oxides: highly selective alkenylation and direct arylation with unactivated arenes.

Authors:  Seung Hwan Cho; Seung Jun Hwang; Sukbok Chang
Journal:  J Am Chem Soc       Date:  2008-06-27       Impact factor: 15.419

9.  Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine.

Authors:  Alexandre Larivée; James J Mousseau; André B Charette
Journal:  J Am Chem Soc       Date:  2007-12-08       Impact factor: 15.419

10.  Rh(I)-catalyzed arylation of heterocycles via C-H bond activation: expanded scope through mechanistic insight.

Authors:  Jared C Lewis; Ashley M Berman; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2008-02-02       Impact factor: 15.419
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  19 in total

1.  C-H arylation of pyridines: high regioselectivity as a consequence of the electronic character of C-H bonds and heteroarene ring.

Authors:  Pengfei Guo; Jung Min Joo; Souvik Rakshit; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2011-09-22       Impact factor: 15.419

2.  Rh(I)-catalyzed direct arylation of azines.

Authors:  Ashley M Berman; Robert G Bergman; Jonathan A Ellman
Journal:  J Org Chem       Date:  2010-10-29       Impact factor: 4.354

3.  C-H and C-N Activation at Redox-Active Pyridine Complexes of Iron.

Authors:  K Cory MacLeod; Richard A Lewis; Daniel E DeRosha; Brandon Q Mercado; Patrick L Holland
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-21       Impact factor: 15.336

4.  Direct C-H arylation of electron-deficient heterocycles with arylboronic acids.

Authors:  Ian B Seiple; Shun Su; Rodrigo A Rodriguez; Ryan Gianatassio; Yuta Fujiwara; Adam L Sobel; Phil S Baran
Journal:  J Am Chem Soc       Date:  2010-09-29       Impact factor: 15.419

5.  C-H bonds as ubiquitous functionality: preparation of multiple regioisomers of arylated 1,2,4-triazoles via C-H arylation.

Authors:  Jung Min Joo; Pengfei Guo; Dalibor Sames
Journal:  J Org Chem       Date:  2012-12-31       Impact factor: 4.354

6.  Radical-based regioselective C-H functionalization of electron-deficient heteroarenes: scope, tunability, and predictability.

Authors:  Fionn O'Hara; Donna G Blackmond; Phil S Baran
Journal:  J Am Chem Soc       Date:  2013-07-30       Impact factor: 15.419

7.  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

8.  Chichibabin-type direct alkylation of pyridyl alcohols with alkyl lithium reagents.

Authors:  Jenna L Jeffrey; Richmond Sarpong
Journal:  Org Lett       Date:  2012-10-12       Impact factor: 6.005

9.  Application of Daugulis copper-catalyzed direct arylation to the synthesis of 5-aryl benzotriazepines.

Authors:  Sirilata Yotphan; Robert G Bergman; Jonathan A Ellman
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

Review 10.  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
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