Literature DB >> 23495912

Regioselective and stereospecific copper-catalyzed aminoboration of styrenes with bis(pinacolato)diboron and O-benzoyl-N,N-dialkylhydroxylamines.

Naoki Matsuda1, Koji Hirano, Tetsuya Satoh, Masahiro Miura.   

Abstract

A Cu-catalyzed regioselective and stereospecific aminoboration of styrenes with bis(pinacolato)diboron and O-benzoyl-N,N-dialkylhydroxylamines that delivers the corresponding β-aminoalkylboranes in good yields has been developed. The Cu catalysis enables introduction of both amine and boron moieties to C-C double bonds simultaneously in a syn fashion. Moreover, the use of a chiral biphosphine ligand, (S,S)-Me-Duphos, provides a catalytic enantioselective route to optically active β-aminoalkylboranes.

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Year:  2013        PMID: 23495912     DOI: 10.1021/ja4007645

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


  30 in total

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Journal:  Org Lett       Date:  2015-02-02       Impact factor: 6.005

2.  A Modified System for the Synthesis of Enantioenriched N-Arylamines through Copper-Catalyzed Hydroamination.

Authors:  Saki Ichikawa; Shaolin Zhu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-12       Impact factor: 15.336

3.  Enantio- and Diastereoselective 1,2-Additions to α-Ketoesters with Diborylmethane and Substituted 1,1-Diborylalkanes.

Authors:  Stephanie A Murray; Jacob C Green; Sanita B Tailor; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-20       Impact factor: 15.336

Review 4.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

5.  Mechanism-based enhancement of scope and enantioselectivity for reactions involving a copper-substituted stereogenic carbon centre.

Authors:  Jaehee Lee; Suttipol Radomkit; Sebastian Torker; Juan Del Pozo; Amir H Hoveyda
Journal:  Nat Chem       Date:  2017-10-02       Impact factor: 24.427

6.  Cu-Catalyzed Asymmetric Aminoboration of E-Vinylarenes with pivZPhos as the Ligand.

Authors:  Linglin Wu; Olga Zatolochnaya; Bo Qu; Ling Wu; Lucille A Wells; Marisa C Kozlowski; Chris H Senanayake; Jinhua J Song; Yongda Zhang
Journal:  Org Lett       Date:  2019-10-24       Impact factor: 6.005

7.  CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.

Authors:  Richard Y Liu; Stephen L Buchwald
Journal:  Acc Chem Res       Date:  2020-05-13       Impact factor: 22.384

8.  Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.

Authors:  Scott A Shuler; Guoyin Yin; Sarah B Krause; Caroline M Vesper; Donald A Watson
Journal:  J Am Chem Soc       Date:  2016-10-18       Impact factor: 15.419

9.  Enantio- and regioselective CuH-catalyzed hydroamination of alkenes.

Authors:  Shaolin Zhu; Nootaree Niljianskul; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2013-10-15       Impact factor: 15.419

10.  Catalytic Carbo- and Aminoboration of Alkenyl Carbonyl Compounds via Five- and Six-Membered Palladacycles.

Authors:  Zhen Liu; Hui-Qi Ni; Tian Zeng; Keary M Engle
Journal:  J Am Chem Soc       Date:  2018-02-07       Impact factor: 15.419

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