Literature DB >> 31165124

(Hetero)arylboration of alkynes: a strategy for the synthesis of α,α-bis(hetero)arylketones.

Yuan Huang1, Allison M Bergmann, M Kevin Brown.   

Abstract

A method for (hetero)arylboration of alkynes is presented. The reaction allows for the synthesis of densely functionalized tetrasubstituted alkenes with control of regioselectivity and diastereoselectivity. The conversion of the products to the corresponding α,α-bis(hetero)arylketones is also shown.

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Year:  2019        PMID： 31165124      PMCID： PMC6823596          DOI： 10.1039/c9ob00961b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  18 in total

1.  Diboron(4) Compounds: From Structural Curiosity to Synthetic Workhorse.

Authors:  Emily C Neeve; Stephen J Geier; Ibraheem A I Mkhalid; Stephen A Westcott; Todd B Marder
Journal:  Chem Rev       Date:  2016-07-19       Impact factor: 60.622

2.  Alkene carboboration enabled by synergistic catalysis.

Authors:  Kevin B Smith; Kaitlyn M Logan; Wei You; M Kevin Brown
Journal:  Chemistry       Date:  2014-08-11       Impact factor: 5.236

3.  Copper-catalyzed cross-coupling of boronic esters with aryl iodides and application to the carboboration of alkynes and allenes.

Authors:  Yiqing Zhou; Wei You; Kevin B Smith; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-24       Impact factor: 15.336

4.  Catalyst-Controlled 1,2- and 1,1-Arylboration of α-Alkyl Alkenyl Arenes.

Authors:  Allison M Bergmann; Stanna K Dorn; Kevin B Smith; Kaitlyn M Logan; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-09       Impact factor: 15.336

5.  Copper-Catalyzed Synthesis of Tetrasubstituted Enynylboronates via Chemo-, Regio-, and Stereoselective Borylalkynylation.

Authors:  Jung Tae Han; Jaesook Yun
Journal:  Org Lett       Date:  2018-03-21       Impact factor: 6.005

6.  Silicon-tethered strategy for copper(I)-catalyzed stereo- and regioselective alkylboration of alkynes.

Authors:  Koji Kubota; Hiroaki Iwamoto; Eiji Yamamoto; Hajime Ito
Journal:  Org Lett       Date:  2015-01-20       Impact factor: 6.005

7.  Arylboration of alkenes by cooperative palladium/copper catalysis.

Authors:  Kazuhiko Semba; Yoshiaki Nakao
Journal:  J Am Chem Soc       Date:  2014-05-14       Impact factor: 15.419

8.  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

9.  Ligand-Enabled, Copper-Catalyzed Regio- and Stereoselective Synthesis of Trialkylsubstituted Alkenylboronates from Unactivated Internal Alkynes.

Authors:  Taisuke Itoh; Yohei Shimizu; Motomu Kanai
Journal:  J Am Chem Soc       Date:  2016-06-09       Impact factor: 15.419

10.  Copper(I)-catalyzed formal carboboration of alkynes: synthesis of tri- and tetrasubstituted vinylboronates.

Authors:  Ricardo Alfaro; Alejandro Parra; José Alemán; José Luis García Ruano; Mariola Tortosa
Journal:  J Am Chem Soc       Date:  2012-09-07       Impact factor: 15.419
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  1 in total

1.  Cooperative Pd/Cu Catalysis for Alkene Arylboration: Opportunities for Divergent Reactivity.

Authors:  Stanna K Dorn; M Kevin Brown
Journal:  ACS Catal       Date:  2022-01-24       Impact factor: 13.700
  1 in total

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