Literature DB >> 23641126

The Use of Tertiary Alkylmagnesium Nucleophiles in Ni-Catalyzed Cross-Coupling Reactions.

Amruta Joshi-Pangu1, Mark R Biscoe.   

Abstract

Nickel-catalyzed cross-coupling reactions of unactivated tertiary alkyl nucleophiles and aryl bromides have been developed using N-heterocyclic carbene ligands. These processes are reviewed alongside earlier attempts to employ unactivated tertiary alkyl nucleophiles in cross-coupling reactions. Potential mechanisms for the transformations, and future challenges in this field are discussed.

Entities:  

Keywords:  Grignard reaction; cross-coupling; homogeneous catalysis; nickel; transition metals

Year:  2012        PMID： 23641126      PMCID： PMC3639446          DOI： 10.1055/s-0031-1290765

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  32 in total

1.  Nickel-catalyzed Negishi cross-couplings of secondary nucleophiles with secondary propargylic electrophiles at room temperature.

Authors:  Sean W Smith; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  A general and selective copper-catalyzed cross-coupling of tertiary Grignard reagents with azacyclic electrophiles.

Authors:  Lukas Hintermann; Li Xiao; Aurélie Labonne
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Nickel-catalyzed cross-coupling of aryl bromides with tertiary Grignard reagents utilizing donor-functionalized N-heterocyclic carbenes (NHCs).

Authors:  Claudia Lohre; Thomas Dröge; Congyang Wang; Frank Glorius
Journal:  Chemistry       Date:  2011-04-20       Impact factor: 5.236

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.  Computational explorations of mechanisms and ligand-directed selectivities of copper-catalyzed Ullmann-type reactions.

Authors:  Gavin O Jones; Peng Liu; K N Houk; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

6.  Highly diastereoselective C(sp3)-C(sp) cross-coupling reactions between 1,3- and 1,4-substituted cyclohexylzinc reagents and bromoalkynes through remote stereocontrol.

Authors:  Tobias Thaler; Li-Na Guo; Peter Mayer; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-01       Impact factor: 15.336

7.  A new aspect of nickel-catalyzed Grignard cross-coupling reactions: selective synthesis, structure, and catalytic behavior of a T-shape three-coordinate nickel(I) chloride bearing a bulky NHC ligand.

Authors:  Satoshi Miyazaki; Yuji Koga; Taisuke Matsumoto; Kouki Matsubara
Journal:  Chem Commun (Camb)       Date:  2010-02-11       Impact factor: 6.222

8.  Enantioselective, palladium-catalyzed alpha-arylation of N-Boc-pyrrolidine.

Authors:  Kevin R Campos; Artis Klapars; Jacob H Waldman; Peter G Dormer; Cheng-yi Chen
Journal:  J Am Chem Soc       Date:  2006-03-22       Impact factor: 15.419

9.  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

10.  Direct aminoalkylation of arenes and hetarenes via Ni-catalyzed Negishi cross-coupling reactions.

Authors:  Laurin Melzig; Andrey Gavryushin; Paul Knochel
Journal:  Org Lett       Date:  2007-11-30       Impact factor: 6.005
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  6 in total

1.  Palladium-catalyzed borylation of primary alkyl bromides.

Authors:  Amruta Joshi-Pangu; Xinghua Ma; Mohamed Diane; Sidra Iqbal; Robert J Kribs; Richard Huang; Chao-Yuan Wang; Mark R Biscoe
Journal:  J Org Chem       Date:  2012-07-23       Impact factor: 4.354

2.  Stereospecific Palladium-Catalyzed Acylation of Enantioenriched Alkylcarbastannatranes: A General Alternative to Asymmetric Enolate Reactions.

Authors:  Chao-Yuan Wang; Glenn Ralph; Joseph Derosa; Mark R Biscoe
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-16       Impact factor: 15.336

3.  Nickel-Catalyzed Cross-Coupling of Vinyl Dioxanones to Form Enantiomerically Enriched Cyclopropanes.

Authors:  Yi-An Guo; Tao Liang; Seung Wook Kim; Hongde Xiao; Michael J Krische
Journal:  J Am Chem Soc       Date:  2017-05-10       Impact factor: 15.419

4.  Stereoretentive Pd-catalysed Stille cross-coupling reactions of secondary alkyl azastannatranes and aryl halides.

Authors:  Ling Li; Chao-Yuan Wang; Rongcai Huang; Mark R Biscoe
Journal:  Nat Chem       Date:  2013-05-19       Impact factor: 24.427

5.  Construction of congested Csp3-Csp3 bonds by a formal Ni-catalyzed alkylboration.

Authors:  Amit Kumar Simlandy; Stephen R Sardini; M Kevin Brown
Journal:  Chem Sci       Date:  2021-03-09       Impact factor: 9.825

6.  Stereospecific pd-catalyzed cross-coupling reactions of secondary alkylboron nucleophiles and aryl chlorides.

Authors:  Ling Li; Shibin Zhao; Amruta Joshi-Pangu; Mohamed Diane; Mark R Biscoe
Journal:  J Am Chem Soc       Date:  2014-09-23       Impact factor: 15.419
  6 in total

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