Literature DB >> 19899771

An aromatic Glaser-Hay reaction.

Hien-Quang Do1, Olafs Daugulis.   

Abstract

A general method for copper-catalyzed deprotonative dimerization of arenes by employing oxygen as the terminal oxidant has been developed. Electron-rich and electron-poor heterocycles as well as electron-poor arenes are reactive. The method is tolerant to functionalities such as nitro, cyano, dialkylamino, and ester groups.

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Year:  2009        PMID： 19899771      PMCID： PMC2791693          DOI： 10.1021/ja907479j

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


  29 in total

Review 1.  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

2.  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

3.  Copper-catalyzed aerobic phosphonation of sp3 C-H bonds.

Authors:  Olivier Baslé; Chao-Jun Li
Journal:  Chem Commun (Camb)       Date:  2009-06-05       Impact factor: 6.222

4.  CuBr-catalyzed direct indolation of tetrahydroisoquinolines via cross-dehydrogenative coupling between sp3 C-H and sp2 C-H bonds.

Authors:  Zhiping Li; Chao-Jun Li
Journal:  J Am Chem Soc       Date:  2005-05-18       Impact factor: 15.419

5.  Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules.

Authors:  Louis-Charles Campeau; Keith Fagnou
Journal:  Chem Commun (Camb)       Date:  2006-01-30       Impact factor: 6.222

6.  Copper-catalyzed aerobic oxidative amidation of terminal alkynes: efficient synthesis of ynamides.

Authors:  Tetsuya Hamada; Xuan Ye; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2008-01-01       Impact factor: 15.419

7.  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

8.  Copper-catalyzed "click" reaction/direct arylation sequence: modular syntheses of 1,2,3-triazoles.

Authors:  Lutz Ackermann; Harish K Potukuchi; Dirk Landsberg; Rubén Vicente
Journal:  Org Lett       Date:  2008-06-13       Impact factor: 6.005

9.  Copper(I)-mediated oxidative cross-coupling between functionalized alkynyl lithium and aryl magnesium reagents.

Authors:  Srinivas Reddy Dubbaka; Marcel Kienle; Herbert Mayr; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

10.  TMPZnCl.LiCl: a new active selective base for the directed zincation of sensitive aromatics and heteroaromatics.

Authors:  Marc Mosrin; Paul Knochel
Journal:  Org Lett       Date:  2009-04-16       Impact factor: 6.005
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  11 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

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.  Copper-catalyzed cyanation of heterocycle carbon-hydrogen bonds.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

4.  Cobalt-promoted dimerization of aminoquinoline benzamides.

Authors:  Liene Grigorjeva; Olafs Daugulis
Journal:  Org Lett       Date:  2015-02-17       Impact factor: 6.005

5.  Copper-Catalyzed Homo-Dimerization of Nitronates and Enolates under Oxygen Atmosphere.

Authors:  Hien-Quang Do; Hung Tran-Vu; Olafs Daugulis
Journal:  Organometallics       Date:  2012-06-21       Impact factor: 3.876

6.  Palladium-catalyzed indole, pyrrole, and furan arylation by aryl chlorides.

Authors:  Enrico T Nadres; Anna Lazareva; Olafs Daugulis
Journal:  J Org Chem       Date:  2010-12-30       Impact factor: 4.354

7.  Nickel, manganese, cobalt, and iron-catalyzed deprotonative arene dimerization.

Authors:  Thanh Truong; Joseph Alvarado; Ly Dieu Tran; Olafs Daugulis
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

8.  Copper-promoted sulfenylation of sp2 C-H bonds.

Authors:  Ly Dieu Tran; Ilya Popov; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2012-10-29       Impact factor: 15.419

Review 9.  Developing ligands for palladium(II)-catalyzed C-H functionalization: intimate dialogue between ligand and substrate.

Authors:  Keary M Engle; Jin-Quan Yu
Journal:  J Org Chem       Date:  2013-05-03       Impact factor: 4.354

10.  General method for functionalized polyaryl synthesis via aryne intermediates.

Authors:  Thanh Truong; Milad Mesgar; Ky Khac Anh Le; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2014-06-03       Impact factor: 15.419
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