Literature DB >> 26242903

Enantioselective ortho-C-H cross-coupling of diarylmethylamines with organoborons.

Brian N Laforteza1, Kelvin S L Chan1, Jin-Quan Yu2.   

Abstract

The commonly used para-nitrobenzenesulfonyl (nosyl) protecting group is employed to direct the CH activation of amines for the first time. An enantioselective ortho-CH cross-coupling between nosyl-protected diarylmethylamines and arylboronic acid pinacol esters has been achieved utilizing chiral mono-N-protected amino acid (MPAA) ligands as a promoter.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; CH coupling; amino acid ligands; enantioselective catalysis; palladium

Mesh：

Substances：

Year:  2015        PMID： 26242903      PMCID： PMC4642891          DOI： 10.1002/anie.201505204

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  37 in total

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8.  Pd-catalyzed enantioselective C-H iodination: asymmetric synthesis of chiral diarylmethylamines.

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  9 in total

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2.  Ligand-Promoted meta-C-H Functionalization of Benzylamines.

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Journal:  Angew Chem Int Ed Engl       Date:  2017-03-30       Impact factor: 15.336

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5.  Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling.

Authors:  Byoungmoo Kim; Alex J Chinn; Daniel R Fandrick; Chris H Senanayake; Robert A Singer; Scott J Miller
Journal:  J Am Chem Soc       Date:  2016-06-15       Impact factor: 15.419

6.  Ligand-Enabled meta-Selective C-H Arylation of Nosyl-Protected Phenethylamines, Benzylamines, and 2-Aryl Anilines.

Authors:  Qiuping Ding; Shengqing Ye; Guolin Cheng; Peng Wang; Marcus E Farmer; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2016-12-23       Impact factor: 15.419

7.  Desymmetrization of Diarylmethylamido Bis(phenols) through Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2 amu Alteration at an Achiral Residue within the Catalyst.

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8.  Peptide-Based Catalysts Reach the Outer Sphere through Remote Desymmetrization and Atroposelectivity.

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9.  Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines.

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  9 in total

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