Literature DB >> 19219972

Steric modulation of chiral biaryl diamines via Pd-catalyzed directed C-H arylation.

Christopher C Scarborough1, Richard I McDonald, Caroline Hartmann, Graham T Sazama, Ana Bergant, Shannon S Stahl.   

Abstract

Palladium-catalyzed directed arylation of 2,2'-diacetamidobiaryls with aryl iodides provides efficient access to chiral ortho-substituted biaryl diamines. Aryl iodides with para- and meta-substituents are tolerated. Deprotection of the acetyl groups under basic conditions furnishes the free diamines, which should find broad utility in asymmetric catalysis.

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Year:  2009        PMID： 19219972      PMCID： PMC2726659          DOI： 10.1021/jo802632v

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  21 in total

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Journal:  J Org Chem       Date:  2004-04-30       Impact factor: 4.354

2.  Anilide ortho-arylation by using C-H activation methodology.

Authors:  Olafs Daugulis; Vladimir G Zaitsev
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3.  Enantioselective aziridination using copper complexes of biaryl Schiff bases.

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4.  Oxidative C-H activation/C-C bond forming reactions: synthetic scope and mechanistic insights.

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Journal:  J Am Chem Soc       Date:  2005-05-25       Impact factor: 15.419

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Journal:  J Org Chem       Date:  2007-02-21       Impact factor: 4.354

6.  Bidentate carbenoid ester coordination in ruthenium(II) Schiff-base complexes leading to excellent levels of diastereo- and enantioselectivity in catalytic alkene cyclopropanation.

Authors:  I J Munslow; K M Gillespie; R J Deeth; P Scott
Journal:  Chem Commun (Camb)       Date:  2001-09-07       Impact factor: 6.222

7.  Palladium-catalyzed anilide ortho-arylation and subsequent one-pot cyclization to phenanthridines.

Authors:  Dmitry Shabashov; Olafs Daugulis
Journal:  J Org Chem       Date:  2007-09-07       Impact factor: 4.354

8.  Asymmetric Morita-Baylis-Hillman reaction of arylaldehydes with 2-cyclohexen-1-one catalyzed by chiral bis(thio)urea and DABCO.

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Journal:  Org Lett       Date:  2008-02-20       Impact factor: 6.005

9.  Chiral biarylamido/anisole complexes of yttrium in enantioselective aminoalkene hydaroamination/cyclisation.

Authors:  Paul N O'Shaughnessy; Kevin M Gillespie; Paul D Knight; Ian J Munslow; Peter Scott
Journal:  Dalton Trans       Date:  2004-06-28       Impact factor: 4.390

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Authors:  Mikihiro Takasaki; Yukihiro Motoyama; Seong-Ho Yoon; Isao Mochida; Hideo Nagashima
Journal:  J Org Chem       Date:  2007-11-29       Impact factor: 4.354
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  8 in total

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Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Aldrichimica Acta       Date:  2012-01-01       Impact factor: 3.667

2.  Structural, Mechanistic, Spectroscopic, and Preparative Studies on the Lewis Base Catalyzed, Enantioselective Sulfenofunctionalization of Alkenes.

Authors:  Eduard Hartmann; Scott E Denmark
Journal:  Helv Chim Acta       Date:  2017-09-14       Impact factor: 2.164

3.  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

4.  Direct intermolecular aniline ortho-arylation via benzyne intermediates.

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Journal:  Org Lett       Date:  2012-11-13       Impact factor: 6.005

5.  Room temperature C-H activation and cross-coupling of aryl ureas in water.

Authors:  Takashi Nishikata; Alexander R Abela; Bruce H Lipshutz
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6.  Synthesis of Pd Complexes Bearing an Enantiomerically-Resolved Seven-Membered N-Heterocyclic Carbene Ligands and Initial Studies of their Use in Asymmetric Wacker-Type Oxidative Cyclization Reactions.

Authors:  Christopher C Scarborough; Ana Bergant; Graham T Sazama; Ilia A Guzei; Lara C Spencer; Shannon S Stahl
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

Review 7.  Palladium catalyzed allylic C-H alkylation: a mechanistic perspective.

Authors:  Casper Junker Engelin; Peter Fristrup
Journal:  Molecules       Date:  2011-01-21       Impact factor: 4.411

8.  Cationic Pd(II)-catalyzed C-H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies.

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  8 in total

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