Literature DB >> 22540212

Cross coupling between sp3-carbon and sp3-carbon using a diborylmethane derivative at room temperature.

Kohei Endo1, Takahiro Ohkubo, Takafumi Ishioka, Takanori Shibata.   

Abstract

A novel example of the Suzuki-Miyaura cross-coupling reaction between sp(3)-carbon and sp(3)-carbon is described. The reaction of a diborylmethane derivative with allyl halides or benzyl halides proceeded efficiently in the presence of appropriate Pd-catalysts at room temperature. The present approaches provide functionalized homoallylboronates and alkylboronates with excellent regio- and chemoselectivities.

Entities:  

Year:  2012        PMID: 22540212     DOI: 10.1021/jo3004293

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  7 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.  Enantio- and Diastereoselective Synthesis of Hydroxy Bis(boronates) via Cu-Catalyzed Tandem Borylation/1,2-Addition.

Authors:  Jacob C Green; Matthew V Joannou; Stephanie A Murray; Joseph M Zanghi; Simon J Meek
Journal:  ACS Catal       Date:  2017-05-25       Impact factor: 13.084

4.  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

5.  A catalytic enantiotopic-group-selective Suzuki reaction for the construction of chiral organoboronates.

Authors:  Chunrui Sun; Bowman Potter; James P Morken
Journal:  J Am Chem Soc       Date:  2014-02-24       Impact factor: 15.419

6.  Simple access to elusive α-boryl carbanions and their alkylation: an umpolung construction for organic synthesis.

Authors:  Kai Hong; Xun Liu; James P Morken
Journal:  J Am Chem Soc       Date:  2014-07-16       Impact factor: 15.419

7.  Nonracemic allylic boronates through enantiotopic-group-selective cross-coupling of geminal bis(boronates) and vinyl halides.

Authors:  Bowman Potter; Adam A Szymaniak; Emma K Edelstein; James P Morken
Journal:  J Am Chem Soc       Date:  2014-12-15       Impact factor: 15.419

  7 in total

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