Literature DB >> 16092880

The first Negishi cross-coupling reaction of two alkyl centers utilizing a Pd-N-heterocyclic carbene (NHC) catalyst.

Niloufar Hadei1, Eric Assen B Kantchev, Christopher J O'Brien, Michael G Organ.   

Abstract

The development of an NHC-based system capable of cross-coupling sp(3)-sp(3) centers in high yield has been a long-standing challenge. This communication describes the use of a Pd-NHC catalytic system that achieves room-temperature Negishi cross-couplings of unactivated, primary bromides and alkyl organozinc reagents with a variety of functionality. [reaction: see text]

Entities:  

Year:  2005        PMID: 16092880     DOI: 10.1021/ol0514909

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


  13 in total

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Review 2.  Nickel-catalyzed cross-couplings involving carbon-oxygen bonds.

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

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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.  Highly diastereoselective Csp₃-Csp₂ Negishi cross-coupling with 1,2-, 1,3- and 1,4-substituted cycloalkylzinc compounds.

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7.  A Robust Dimethylgold(III) Complex Stabilized by a 2-Pyridyl-2-pyrrolide Ligand.

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8.  Stereoselective synthesis of dienyl-carboxylate building blocks: formal synthesis of inthomycin C.

Authors:  Caroline Souris; Frédéric Frébault; Ashay Patel; Davide Audisio; K N Houk; Nuno Maulide
Journal:  Org Lett       Date:  2013-06-13       Impact factor: 6.005

9.  Total syntheses of (-)-alpha-kainic acid and (+)-alpha-allokainic acid via stereoselective C-H insertion and efficient 3,4-stereocontrol.

Authors:  Young Chun Jung; Cheol Hwan Yoon; Edward Turos; Kyung Soo Yoo; Kyung Woon Jung
Journal:  J Org Chem       Date:  2007-11-29       Impact factor: 4.354

10.  Total synthesis of the anti-inflammatory and pro-resolving lipid mediator MaR1n-3 DPA utilizing an sp(3) -sp(3) Negishi cross-coupling reaction.

Authors:  Jørn Eivind Tungen; Marius Aursnes; Jesmond Dalli; Hildur Arnardottir; Charles Nicholas Serhan; Trond Vidar Hansen
Journal:  Chemistry       Date:  2014-09-15       Impact factor: 5.236

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