Literature DB >> 12583734

Highly efficient, general procedure for the preparation of alkylzinc reagents from unactivated alkyl bromides and chlorides.

Shouquan Huo1.   

Abstract

[reaction: see text] Alkylzinc bromides have been efficiently prepared by the direct insertion of zinc metal (dust, powder, granule, shot), activated with 1-5 mol % I(2), into alkyl bromides in a polar aprotic solvent. The zinc reagents thus formed undergo Ni- and Pd-catalyzed cross-coupling with aryl halides to produce functionalized alkylarenes in excellent yields.

Entities:  

Year:  2003        PMID: 12583734     DOI: 10.1021/ol0272693

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


  24 in total

Review 1.  Nickel-catalyzed cross-couplings involving carbon-oxygen bonds.

Authors:  Brad M Rosen; Kyle W Quasdorf; Daniella A Wilson; Na Zhang; Ana-Maria Resmerita; Neil K Garg; Virgil Percec
Journal:  Chem Rev       Date:  2010-12-06       Impact factor: 60.622

2.  Synthesis of 5-fluoroalkylated pyrimidine nucleosides via Negishi cross-coupling.

Authors:  Ann-Marie Chacko; Wenchao Qu; Hank F Kung
Journal:  J Org Chem       Date:  2008-06-04       Impact factor: 4.354

3.  Synthesis and in vitro evaluation of 5-[(18)f]fluoroalkyl pyrimidine nucleosides for molecular imaging of herpes simplex virus type 1 thymidine kinase reporter gene expression.

Authors:  Ann-Marie Chacko; Wenchao Qu; Hank F Kung
Journal:  J Med Chem       Date:  2008-09-25       Impact factor: 7.446

Review 4.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

5.  NICKEL-CATALYZED ASYMMETRIC NEGISHI CROSS-COUPLINGS OF RACEMIC SECONDARY ALLYLIC CHLORIDES WITH ALKYLZINCS: (S,E)-ETHYL 6-(1,3-DIOXOLAN-2-YL)-4-METHYLHEX-2-ENOATE.

Authors:  Sha Lou; Gregory C Fu
Journal:  Organic Synth       Date:  2010-01-01

6.  Negishi Cross-Coupling Is Compatible with a Reactive B-Cl Bond: Development of a Versatile Late-Stage Functionalization of 1,2-Azaborines and Its Application to the Synthesis of New BN Isosteres of Naphthalene and Indenyl.

Authors:  Alec N Brown; Bo Li; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2015-07-09       Impact factor: 15.419

7.  11β,17aα-Dihydr-oxy-17aβ-methyl-d-homoandrosta-1,4-diene-3,17-dione monohydrate.

Authors:  Ya Qiu; Ying Chen; Peng Xia
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-03-31

8.  Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven.

Authors:  Dustin S Siegel; Grazia Piizzi; Giovanni Piersanti; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2009-12-18       Impact factor: 4.354

9.  Palladium-catalyzed hydroalkylation of styrenes with organozinc reagents to form carbon-carbon sp3-sp3 bonds under oxidative conditions.

Authors:  Kaveri Balan Urkalan; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2009-12-23       Impact factor: 15.419

10.  syn additions to 4alpha-epoxypyranosides: synthesis of L-idopyranosides.

Authors:  Gang Cheng; Renhua Fan; Jesús M Hernández-Torres; Fabien P Boulineau; Alexander Wei
Journal:  Org Lett       Date:  2007-10-12       Impact factor: 6.005

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