Literature DB >> 24870625

Pd/NHC-catalyzed enantiospecific and regioselective Suzuki-Miyaura arylation of 2-arylaziridines: synthesis of enantioenriched 2-arylphenethylamine derivatives.

Youhei Takeda1, Yuki Ikeda, Akinobu Kuroda, Shino Tanaka, Satoshi Minakata.   

Abstract

A palladium-catalyzed stereospecific and regioselective cross-coupling of enantiopure 2-arylaziridines with arylboronic acids under mild conditions to construct a tertiary stereogenic center has been developed. N-heterocyclic carbene (NHC) ligands efficiently promote the coupling, suppressing β-hydride elimination. The enantiospecific cross-coupling allowed us for preparation of a series of biologically important 2-arylphenethylamine derivatives in an enantiopure form.

Entities:  

Year:  2014        PMID: 24870625     DOI: 10.1021/ja5039616

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


  13 in total

Review 1.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  Synthesis of β-Phenethylamines via Ni/Photoredox Cross-Electrophile Coupling of Aliphatic Aziridines and Aryl Iodides.

Authors:  Talia J Steiman; Junyi Liu; Amanuella Mengiste; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2020-04-06       Impact factor: 15.419

3.  Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Authors:  Louis-Charles Campeau; Nilay Hazari
Journal:  Organometallics       Date:  2018-11-27       Impact factor: 3.876

4.  N-Aminopyridinium reagents as traceless activating groups in the synthesis of N-Aryl aziridines.

Authors:  Hao Tan; Samya Samanta; Asim Maity; Pritam Roychowdhury; David C Powers
Journal:  Nat Commun       Date:  2022-06-10       Impact factor: 17.694

5.  Asymmetric synthesis via stereospecific C-N and C-O bond activation of alkyl amine and alcohol derivatives.

Authors:  Sarah M Pound; Mary P Watson
Journal:  Chem Commun (Camb)       Date:  2018-10-30       Impact factor: 6.222

6.  A ring expansion strategy towards diverse azaheterocycles.

Authors:  Ruirui Li; Bo Li; Hongpeng Zhang; Cheng-Wei Ju; Ying Qin; Xiao-Song Xue; Dongbing Zhao
Journal:  Nat Chem       Date:  2021-07-19       Impact factor: 24.427

7.  Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides.

Authors:  Ming Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-10-23       Impact factor: 15.419

8.  Catalytic α-Arylation of Imines Leading to N-Unprotected Indoles and Azaindoles.

Authors:  Enrico Marelli; Martin Corpet; Yury Minenkov; Rifahath M Neyyappadath; Alessandro Bismuto; Giulia Buccolini; Massimiliano Curcio; Luigi Cavallo; Steven P Nolan
Journal:  ACS Catal       Date:  2016-03-30       Impact factor: 13.084

9.  β-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp)-H bonds using a palladium catalyst.

Authors:  Jing Peng; Chao Chen; Chanjuan Xi
Journal:  Chem Sci       Date:  2015-11-11       Impact factor: 9.825

10.  Stereospecific cross-coupling reactions of aryl-substituted tetrahydrofurans, tetrahydropyrans, and lactones.

Authors:  Emily J Tollefson; David D Dawson; Charlotte A Osborne; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2014-10-13       Impact factor: 15.419

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