Literature DB >> 24810227

Arylboration of alkenes by cooperative palladium/copper catalysis.

Kazuhiko Semba1, Yoshiaki Nakao.   

Abstract

Arylboration of vinylarenes and methyl crotonate with aryl halides and bis(pinacolato)diboron by cooperative Pd/Cu catalysis has been developed, giving 2-boryl-1,1-diarylethanes and an α-aryl-β-boryl ester in a regioselective manner. The reaction is compatible with a variety of functionalities and amenable to be scaled-up to a gram scale with no detriment to the yield. A short synthesis of the biologically active compound CDP840 was performed using the present reaction as a key step.

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Year:  2014        PMID: 24810227     DOI: 10.1021/ja5029556

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


  37 in total

1.  A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal.

Authors:  Xun Liu; T Maxwell Deaton; Fredrik Haeffner; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-09       Impact factor: 15.336

2.  Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.

Authors:  Zhen Liu; Yang Gao; Tian Zeng; Keary M Engle
Journal:  Isr J Chem       Date:  2019-09-10       Impact factor: 3.333

3.  Differential Dihydrofunctionalization of Terminal Alkynes: Synthesis of Benzylic Alkyl Boronates through Reductive Three-Component Coupling.

Authors:  Megan K Armstrong; Gojko Lalic
Journal:  J Am Chem Soc       Date:  2019-04-03       Impact factor: 15.419

Review 4.  Palladium(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol by a Chiral Auxiliary.

Authors:  Zhen Liu; Jiahao Chen; Hou-Xiang Lu; Xiaohan Li; Yang Gao; John R Coombs; Matthew J Goldfogel; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-08       Impact factor: 15.336

5.  Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.

Authors:  Kaitlyn M Logan; Stephen R Sardini; Sean D White; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-12-22       Impact factor: 15.419

6.  Copper-Catalyzed Borylacylation of Activated Alkenes with Acid Chlorides.

Authors:  Yuan Huang; Kevin B Smith; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-18       Impact factor: 15.336

7.  A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.

Authors:  Stig D Friis; Michael T Pirnot; Lauren N Dupuis; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-16       Impact factor: 15.336

8.  Stereospecific Synthesis of E-Alkenes through Anti-Markovnikov Hydroalkylation of Terminal Alkynes.

Authors:  Avijit Hazra; Jason Chen; Gojko Lalic
Journal:  J Am Chem Soc       Date:  2019-08-02       Impact factor: 15.419

9.  Synthesis of Bisheteroarylalkanes by Heteroarylboration: Development and Application of a Pyridylidene-Copper Complex.

Authors:  Yuan Huang; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-27       Impact factor: 15.336

10.  Organoboron chemistry comes to light: recent advances in photoinduced synthetic approaches to organoboron compounds.

Authors:  Viet D Nguyen; Vu T Nguyen; Shengfei Jin; Hang T Dang; Oleg V Larionov
Journal:  Tetrahedron       Date:  2018-12-24       Impact factor: 2.457

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