Literature DB >> 16497011

Triphenylphosphine as a ligand for room-temperature Ni(0)-catalyzed cross-coupling reactions of aryl chlorides with arylboronic acids.

Zhen-Yu Tang1, Qiao-Sheng Hu.   

Abstract

Room-temperature Ni(0)-catalyzed cross-coupling reactions of deactivated aryl chlorides with arylboronic acids with inexpensive triphenylphosphine (PPh3) as a supporting ligand have been accomplished in good to excellent yields. Air-stable Ni(PPh3)2Cl2 has also been established as catalyst precursor, and highly active nickel catalysts were obtained when the reduction of Ni(PPh3)2Cl2 with n-BuLi was carried out in the presence of an aryl chloride.

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Year:  2006        PMID： 16497011      PMCID： PMC2531206          DOI： 10.1021/jo052369i

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  15 in total

1.  An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature.

Authors:  Gereon Altenhoff; Richard Goddard; Christian W Lehmann; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2003-08-11       Impact factor: 15.336

2.  A rationally designed universal catalyst for Suzuki-Miyaura coupling processes.

Authors:  Shawn D Walker; Timothy E Barder; Joseph R Martinelli; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2004-03-26       Impact factor: 15.336

3.  Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Authors:  Timothy E Barder; Shawn D Walker; Joseph R Martinelli; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

4.  Simple (imidazol-2-ylidene)-Pd-acetate complexes as effective precatalysts for sterically hindered Suzuki-Miyaura couplings.

Authors:  Rohit Singh; Mihai S Viciu; Natalia Kramareva; Oscar Navarro; Steven P Nolan
Journal:  Org Lett       Date:  2005-04-28       Impact factor: 6.005

5.  Synthesis of Biaryls via a Nickel(0)-Catalyzed Cross-Coupling Reaction of Chloroarenes with Arylboronic Acids.

Authors:  Syun Saito; Saori Oh-Tani; Norio Miyaura
Journal:  J Org Chem       Date:  1997-11-14       Impact factor: 4.354

6.  Macromolecular effect: synthesis of a ferrocenylmethylphosphine-containing polymer as highly efficient ligands for room-temperature palladium(0)-catalyzed Suzuki cross-coupling reactions of aryl chlorides.

Authors:  Qiao-Sheng Hu; Yong Lu; Zhen-Yu Tang; Hong-Bin Yu
Journal:  J Am Chem Soc       Date:  2003-03-12       Impact factor: 15.419

7.  NiCl(2)(dppe)-catalyzed cross-coupling of aryl mesylates, arenesulfonates, and halides with arylboronic acids.

Authors:  Virgil Percec; Geoffrey M Golding; Jan Smidrkal; Oliver Weichold
Journal:  J Org Chem       Date:  2004-05-14       Impact factor: 4.354

8.  N-heterocyclic carbenes: a new concept in organometallic catalysis.

Authors:  Wolfgang A Herrmann
Journal:  Angew Chem Int Ed Engl       Date:  2002-04-15       Impact factor: 15.336

9.  A general method for the Suzuki-Miyaura cross-coupling of sterically hindered aryl chlorides: synthesis of di- and tri-ortho-substituted biaryls in 2-propanol at room temperature.

Authors:  Oscar Navarro; Roy A Kelly; Steven P Nolan
Journal:  J Am Chem Soc       Date:  2003-12-31       Impact factor: 15.419

10.  Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C[bond]C, C[bond]N, and C[bond]O bond-forming cross-couplings.

Authors:  Noriyasu Kataoka; Quinetta Shelby; James P Stambuli; John F Hartwig
Journal:  J Org Chem       Date:  2002-08-09       Impact factor: 4.354
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  6 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.  Electron-Poor, Fluoro-Containing Arylboronic Acids as Efficient Coupling Partners for Bis(1,5-cyclooctadiene)nickel(0)/Tricyclohexylphosphine-Catalyzed Cross-Coupling Reactions of Aryl Arenesulfonates.

Authors:  Wen-Bo Chen; Chun-Hui Xing; Jie Dong; Qiao-Sheng Hu
Journal:  Adv Synth Catal       Date:  2016-06-07       Impact factor: 5.837

3.  Nickel-Catalyzed Stille Cross Coupling of C-O Electrophiles.

Authors:  John E A Russell; Emily D Entz; Ian M Joyce; Sharon R Neufeldt
Journal:  ACS Catal       Date:  2019-03-04       Impact factor: 13.084

4.  Simplifying nickel(0) catalysis: an air-stable nickel precatalyst for the internally selective benzylation of terminal alkenes.

Authors:  Eric A Standley; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2013-01-14       Impact factor: 15.419

5.  Phosphinite- and phosphite-based Type I palladacycles as highly active catalysts for addition reactions of arylboronic acids with aldehydes, α,β-unsaturated ketones, α-ketoesters, and aldimines.

Authors:  Ping He; Yong Lu; Qiao-Sheng Hu
Journal:  Tetrahedron Lett       Date:  2007-07-23       Impact factor: 2.415

6.  Highly reactive, single-component nickel catalyst precursor for Suzuki-Miyuara cross-coupling of heteroaryl boronic acids with heteroaryl halides.

Authors:  Shaozhong Ge; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-07       Impact factor: 15.336
  6 in total

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