Literature DB >> 22685029

Higher-order zincates as transmetalators in alkyl-alkyl negishi cross-coupling.

Lucas C McCann1, Howard N Hunter, Jason A C Clyburne, Michael G Organ.   

Abstract

Negishi revisited: higher-order alkyl zincates have been subjected to Negishi coupling with alkyl bromides. For the first time, coupling takes place in straight THF, i.e., without a salt additive and a high dielectric co-solvent. This provides evidence that it is the higher-order zincate that undergoes transmetalation to Pd, and not mono-anionic zincates or any of the other species present in the Schlenk equilibrium.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2012        PMID： 22685029     DOI： 10.1002/anie.201203547

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  9 in total

1.  Palladium-catalyzed completely linear-selective Negishi cross-coupling of allylzinc halides with aryl and vinyl electrophiles.

Authors:  Yang Yang; Thomas J L Mustard; Paul Ha-Yeon Cheong; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-08       Impact factor: 15.336

2.  Nickel-Catalyzed Alkyl-Alkyl Cross-Couplings of Fluorinated Secondary Electrophiles: A General Approach to the Synthesis of Compounds having a Perfluoroalkyl Substituent.

Authors:  Yufan Liang; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-12       Impact factor: 15.336

3.  Catalytic enantioselective cross-couplings of secondary alkyl electrophiles with secondary alkylmetal nucleophiles: Negishi reactions of racemic benzylic bromides with achiral alkylzinc reagents.

Authors:  Jörg T Binder; Christopher J Cordier; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2012-10-05       Impact factor: 15.419

4.  Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Chlorides with Primary Alkyl Chlorides.

Authors:  Seoyoung Kim; Matthew J Goldfogel; Michael M Gilbert; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2020-05-21       Impact factor: 15.419

5.  Highly selective palladium-catalyzed cross-coupling of secondary alkylzinc reagents with heteroaryl halides.

Authors:  Yang Yang; Katrin Niedermann; Chong Han; Stephen L Buchwald
Journal:  Org Lett       Date:  2014-08-25       Impact factor: 6.005

6.  A Ball-Milling-Enabled Reformatsky Reaction.

Authors:  Qun Cao; Roderick T Stark; Ian A Fallis; Duncan L Browne
Journal:  ChemSusChem       Date:  2019-06-05       Impact factor: 8.928

7.  A regioselectively 1,1',3,3'-tetrazincated ferrocene complex displaying core and peripheral reactivity.

Authors:  Gordon W Honeyman; David R Armstrong; William Clegg; Eva Hevia; Alan R Kennedy; Ross McLellan; Samantha A Orr; John A Parkinson; Donna L Ramsay; Stuart D Robertson; Stephen Towie; Robert E Mulvey
Journal:  Chem Sci       Date:  2020-03-27       Impact factor: 9.825

8.  Facile Arylation of Four-Coordinate Boron Halides by Borenium Cation Mediated Boro-desilylation and -destannylation.

Authors:  Daniel L Crossley; Jessica Cid; Liam D Curless; Michael L Turner; Michael J Ingleson
Journal:  Organometallics       Date:  2015-12-08       Impact factor: 3.876

9.  Mechanochemical Activation of Zinc and Application to Negishi Cross-Coupling.

Authors:  Qun Cao; Joseph L Howard; Emilie Wheatley; Duncan L Browne
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-02       Impact factor: 15.336
  9 in total

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