Literature DB >> 18763769

Nickel-catalyzed asymmetric cross-couplings of racemic propargylic halides with arylzinc reagents.

Sean W Smith1, Gregory C Fu.   

Abstract

A stereoconvergent method for the catalytic asymmetric Negishi cross-coupling of racemic secondary propargylic halides with arylzinc reagents has been developed. Neither family of compounds has previously been shown to be a suitable partner in such coupling processes. From a practical point of view, it is noteworthy that the catalyst components (NiCl2.glyme and pybox ligand 1) are commercially available.

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Year:  2008        PMID： 18763769      PMCID： PMC2626171          DOI： 10.1021/ja805165y

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  14 in total

1.  Catalysts for cross-coupling reactions with non-activated alkyl halides.

Authors:  Anja C Frisch; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-21       Impact factor: 15.336

2.  Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides.

Authors:  Forrest O Arp; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2005-08-03       Impact factor: 15.419

3.  A room temperature negishi cross-coupling approach to C-alkyl glycosides.

Authors:  Hegui Gong; Riccardo Sinisi; Michel R Gagné
Journal:  J Am Chem Soc       Date:  2007-01-30       Impact factor: 15.419

4.  Asymmetric nickel-catalyzed Negishi cross-couplings of secondary alpha-bromo amides with organozinc reagents.

Authors:  Christian Fischer; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

5.  Catalytic asymmetric Hiyama cross-couplings of racemic alpha-bromo esters.

Authors:  Xing Dai; Neil A Strotman; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2008-02-27       Impact factor: 15.419

6.  Catalyzed asymmetric aryl transfer reactions to aldehydes with boronic acids as aryl source.

Authors:  Carsten Bolm; Jens Rudolph
Journal:  J Am Chem Soc       Date:  2002-12-18       Impact factor: 15.419

7.  Highly efficient ligands for dihydrofolate reductase from Cryptosporidium hominis and Toxoplasma gondii inspired by structural analysis.

Authors:  Phillip M Pelphrey; Veljko M Popov; Tammy M Joska; Jennifer M Beierlein; Erin S D Bolstad; Yale A Fillingham; Dennis L Wright; Amy C Anderson
Journal:  J Med Chem       Date:  2007-02-02       Impact factor: 7.446

8.  Enantioselective alkyl-alkyl Suzuki cross-couplings of unactivated homobenzylic halides.

Authors:  Bunnai Saito; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2008-05-01       Impact factor: 15.419

9.  Ni-catalyzed cascade formation of C(sp3)--C(sp3) bonds by cyclization and cross-coupling reactions of iodoalkanes with alkyl zinc halides.

Authors:  Vilas B Phapale; Elena Buñuel; Miguel García-Iglesias; Diego J Cárdenas
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

10.  Density functional theory studies of negishi alkyl-alkyl cross-coupling reactions catalyzed by a methylterpyridyl-Ni(I) complex.

Authors:  Xufeng Lin; David Lee Phillips
Journal:  J Org Chem       Date:  2008-04-15       Impact factor: 4.354
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  32 in total

Review 1.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  Nickel-Catalyzed Allylic Alkylation with Diarylmethane Pronucleophiles: Reaction Development and Mechanistic Insights.

Authors:  Sheng-Chun Sha; Hui Jiang; Jianyou Mao; Ana Bellomo; Soo A Jeong; Patrick J Walsh
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-03       Impact factor: 15.336

3.  Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates.

Authors:  Meredith S Eno; Alexander Lu; James P Morken
Journal:  J Am Chem Soc       Date:  2016-06-16       Impact factor: 15.419

4.  Catalyst-controlled doubly enantioconvergent coupling of racemic alkyl nucleophiles and electrophiles.

Authors:  Haohua Huo; Bradley J Gorsline; Gregory C Fu
Journal:  Science       Date:  2020-01-31       Impact factor: 47.728

5.  N-Heterocyclic Carbene Bound Nickel(I) Complexes and Their Roles in Catalysis.

Authors:  Kainan Zhang; Martin Conda-Sheridan; Shayna Cooke; Janis Louie
Journal:  Organometallics       Date:  2011-05-09       Impact factor: 3.876

6.  SYNTHESIS OF CHIRAL PYRIDINE BIS(OXAZOLINE) LIGANDS FOR NICKEL-CATALYZED ASYMMETRIC NEGISHI CROSS-COUPLINGS OF SECONDARY ALLYLIC CHLORIDES WITH ALKYLZINCS: 2,6-BIS[(4S)-4,5-DIHYDRO-4-(2-PHENYLETHYL)-2-OXAZOLYL]-PYRIDINE.

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

7.  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

8.  Organozinc Chemistry Enabled by Micellar Catalysis. Palladium-Catalyzed Cross-Couplings between Alkyl and Aryl Bromides in Water at Room Temperature.

Authors:  Christophe Duplais; Arkady Krasovskiy; Bruce H Lipshutz
Journal:  Organometallics       Date:  2011-11-21       Impact factor: 3.876

9.  Nickel/bis(oxazoline)-catalyzed asymmetric Kumada reactions of alkyl electrophiles: cross-couplings of racemic alpha-bromoketones.

Authors:  Sha Lou; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419

10.  Catalytic asymmetric cross-couplings of racemic alpha-bromoketones with arylzinc reagents.

Authors:  Pamela M Lundin; Jorge Esquivias; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
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