Literature DB >> 25436511

Copper-catalyzed/promoted cross-coupling of gem-diborylalkanes with nonactivated primary alkyl halides: an alternative route to alkylboronic esters.

Zhen-Qi Zhang1, Chu-Ting Yang, Lu-Jun Liang, Bin Xiao, Xi Lu, Jing-Hui Liu, Yan-Yan Sun, Todd B Marder, Yao Fu.   

Abstract

The first copper-catalyzed/promoted sp(3)-C Suzuki-Miyaura coupling reaction of gem-diborylalkanes with nonactivated electrophilic reagents is reported. Not only 1, 1-diborylalkanes but also some other gem-diborylalkanes can be coupled with nonactivated primary alkyl halides, offering a new method for sp(3)C-sp(3)C bond formation and, simultaneously, providing a new strategy for the synthesis of alkylboronic esters.

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Year:  2014        PMID: 25436511     DOI: 10.1021/ol503111h

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 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.  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

3.  Catalytic SN2'- and Enantioselective Allylic Substitution with a Diborylmethane Reagent and Application in Synthesis.

Authors:  Ying Shi; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-04       Impact factor: 15.336

4.  Nickel-catalyzed synthesis of 1,1-diborylalkanes from terminal alkenes.

Authors:  Lei Li; Tianjun Gong; Xi Lu; Bin Xiao; Yao Fu
Journal:  Nat Commun       Date:  2017-08-24       Impact factor: 14.919

5.  Insight into Transmetalation Enables Cobalt-Catalyzed Suzuki-Miyaura Cross Coupling.

Authors:  Jamie M Neely; Máté J Bezdek; Paul J Chirik
Journal:  ACS Cent Sci       Date:  2016-12-01       Impact factor: 14.553

6.  Cu-Catalyzed Decarboxylative Borylation.

Authors:  Jie Wang; Ming Shang; Helena Lundberg; Karla S Feu; Scott J Hecker; Tian Qin; Donna G Blackmond; Phil S Baran
Journal:  ACS Catal       Date:  2018-09-13       Impact factor: 13.084

7.  Cu-catalyzed cross-coupling reactions of vinyl epoxide with organoboron compounds: access to homoallylic alcohols.

Authors:  Xiao-Yu Lu; Jin-Song Li; Jin-Yu Wang; Shi-Qun Wang; Yue-Ming Li; Yu-Jing Zhu; Ran Zhou; Wen-Jing Ma
Journal:  RSC Adv       Date:  2018-12-12       Impact factor: 4.036

8.  Copper-Catalyzed Triboration: Straightforward, Atom-Economical Synthesis of 1,1,1-Triborylalkanes from Terminal Alkynes and HBpin.

Authors:  Xiaocui Liu; Wenbo Ming; Yixiao Zhang; Alexandra Friedrich; Todd B Marder
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-11       Impact factor: 15.336

  8 in total

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