Literature DB >> 19928764

Suzuki-Miyaura coupling of aryl carbamates, carbonates, and sulfamates.

Kyle W Quasdorf1, Michelle Riener, Krastina V Petrova, Neil K Garg.   

Abstract

The first Suzuki-Miyaura cross-couplings of carbamates, carbonates, and sulfamates is described. The method provides a powerful means of using simple derivatives of phenol as precursors to polysubstituted aromatic compounds, as exemplified by a concise synthesis of the anti-inflammatory drug flurbiprofen.

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Year:  2009        PMID: 19928764      PMCID: PMC2801021          DOI: 10.1021/ja906477r

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


  15 in total

1.  Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

Authors:  Jwanro Hassan; Marc Sévignon; Christel Gozzi; Emmanuelle Schulz; Marc Lemaire
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

Review 2.  Selected patented cross-coupling reaction technologies.

Authors:  Jean-Pierre Corbet; Gérard Mignani
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

3.  Devising boron reagents for orthogonal functionalization through Suzuki-Miyaura cross-coupling.

Authors:  Mamoru Tobisu; Naoto Chatani
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Nickel-catalyzed cross-coupling reaction of aryl fluorides and chlorides with grignard reagents under nickel/magnesium bimetallic cooperation.

Authors:  Naohiko Yoshikai; Hiroko Mashima; Eiichi Nakamura
Journal:  J Am Chem Soc       Date:  2005-12-28       Impact factor: 15.419

5.  Exploring new uses for C-H amination: Ni-catalyzed cross-coupling of cyclic sulfamates.

Authors:  Paul M Wehn; J Du Bois
Journal:  Org Lett       Date:  2005-10-13       Impact factor: 6.005

6.  Nickel-catalyzed cross-coupling of aryl methyl ethers with aryl boronic esters.

Authors:  Mamoru Tobisu; Toshiaki Shimasaki; Naoto Chatani
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

7.  Biaryl construction via Ni-catalyzed C-O activation of phenolic carboxylates.

Authors:  Bing-Tao Guan; Yang Wang; Bi-Jie Li; Da-Gang Yu; Zhang-Jie Shi
Journal:  J Am Chem Soc       Date:  2008-10-11       Impact factor: 15.419

8.  Cross-coupling reactions of aryl pivalates with boronic acids.

Authors:  Kyle W Quasdorf; Xia Tian; Neil K Garg
Journal:  J Am Chem Soc       Date:  2008-10-08       Impact factor: 15.419

9.  Fluorination of boronic acids mediated by silver(I) triflate.

Authors:  Takeru Furuya; Tobias Ritter
Journal:  Org Lett       Date:  2009-07-02       Impact factor: 6.005

10.  Hydroxyphosphine ligand for nickel-catalyzed cross-coupling through nickel/magnesium bimetallic cooperation.

Authors:  Naohiko Yoshikai; Hirokazu Matsuda; Eiichi Nakamura
Journal:  J Am Chem Soc       Date:  2009-07-15       Impact factor: 15.419

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  43 in total

1.  Cross-Coupling Reactions of Alkenylsilanols with Fluoroalkylsulfonates: Development and Optimization of a Mild and Stereospecific Coupling Process.

Authors:  Scott E Denmark; Christopher S Regens
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

Review 2.  Nickel-catalyzed cross-couplings involving carbon-oxygen bonds.

Authors:  Brad M Rosen; Kyle W Quasdorf; Daniella A Wilson; Na Zhang; Ana-Maria Resmerita; Neil K Garg; Virgil Percec
Journal:  Chem Rev       Date:  2010-12-06       Impact factor: 60.622

3.  Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

Authors:  Timothy B Boit; Ana S Bulger; Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2020-09-10       Impact factor: 13.084

4.  DFT Investigation of Suzuki-Miyaura Reactions with Aryl Sulfamates Using a Dialkylbiarylphosphine-Ligated Palladium Catalyst.

Authors:  Patrick R Melvin; Ainara Nova; David Balcells; Nilay Hazari; Mats Tilset
Journal:  Organometallics       Date:  2017-09-13       Impact factor: 3.876

5.  Cross-coupling of mesylated phenol derivatives with potassium alkoxymethyltrifluoroborates.

Authors:  Gary A Molander; Floriane Beaumard
Journal:  Org Lett       Date:  2011-07-06       Impact factor: 6.005

6.  Scope of the two-step, one-pot palladium-catalyzed borylation/Suzuki cross-coupling reaction utilizing bis-boronic acid.

Authors:  Gary A Molander; Sarah L J Trice; Steven M Kennedy
Journal:  J Org Chem       Date:  2012-09-20       Impact factor: 4.354

7.  Nickel-Catalyzed Stille Cross Coupling of C-O Electrophiles.

Authors:  John E A Russell; Emily D Entz; Ian M Joyce; Sharon R Neufeldt
Journal:  ACS Catal       Date:  2019-03-04       Impact factor: 13.084

8.  Aerobic oxidative Heck/dehydrogenation reactions of cyclohexenones: efficient access to meta-substituted phenols.

Authors:  Yusuke Izawa; Changwu Zheng; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-19       Impact factor: 15.336

9.  Nickel-catalyzed amination of aryl sulfamates and carbamates using an air-stable precatalyst.

Authors:  Liana Hie; Stephen D Ramgren; Tehetena Mesganaw; Neil K Garg
Journal:  Org Lett       Date:  2012-07-31       Impact factor: 6.005

10.  Suzuki-Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene-palladium complex catalyst.

Authors:  Guangming Nan; Fang Ren; Meiming Luo
Journal:  Beilstein J Org Chem       Date:  2010-06-28       Impact factor: 2.883

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