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Literature DB >> 14737321

Practical synthesis of new and highly efficient ligands for the Suzuki reaction of aryl chlorides.

Alexander Zapf¹, Ralf Jackstell, Franck Rataboul, Thomas Riermeier, Axel Monsees, Christa Fuhrmann, Nadim Shaikh, Uwe Dingerdissen, Matthias Beller.

Abstract

A practical synthesis of a novel class of phosphine ligands, phosphino substituted N-aryl pyrroles (PAP ligands), has been developed. These ligands are applied in the palladium-catalyzed coupling of a variety of aryl and heteroaryl chlorides with phenylboronic acid showing exceedingly high turnover numbers at mild reaction temperatures and even at room temperature.

Entities: Chemical

Year: 2003 PMID： 14737321 DOI： 10.1039/b311268n

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

11 in total

Review 1. Carbon-heteroatom bond formation catalysed by organometallic complexes.

Authors: John F Hartwig
Journal: Nature Date: 2008-09-18 Impact factor: 49.962

2. The scope and mechanism of palladium-catalysed Markovnikov alkoxycarbonylation of alkenes.

Authors: Haoquan Li; Kaiwu Dong; Haijun Jiao; Helfried Neumann; Ralf Jackstell; Matthias Beller
Journal: Nat Chem Date: 2016-09-05 Impact factor: 24.427

3. Synthesis of an electron-rich KITPHOS monophosphine, preparation of derived metal complexes and applications in catalysis.

Authors: Simon Doherty; Catherine H Smyth; Julian G Knight; Stephen A K Hashmi
Journal: Nat Protoc Date: 2012-09-20 Impact factor: 13.491

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

Authors: Zhen-Yu Tang; Qiao-Sheng Hu
Journal: J Org Chem Date: 2006-03-03 Impact factor: 4.354

5. Organotrifluoroborates and monocoordinated palladium complexes as catalysts--a perfect combination for Suzuki-Miyaura coupling.

Authors: Gary A Molander; Belgin Canturk
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

6. Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods.

Authors: Peter S Kutchukian; James F Dropinski; Kevin D Dykstra; Bing Li; Daniel A DiRocco; Eric C Streckfuss; Louis-Charles Campeau; Tim Cernak; Petr Vachal; Ian W Davies; Shane W Krska; Spencer D Dreher
Journal: Chem Sci Date: 2016-01-26 Impact factor: 9.825

Practical synthesis of new and highly efficient ligands for the Suzuki reaction of aryl chlorides.

Review 1. Carbon-heteroatom bond formation catalysed by organometallic complexes.

2. The scope and mechanism of palladium-catalysed Markovnikov alkoxycarbonylation of alkenes.

3. Synthesis of an electron-rich KITPHOS monophosphine, preparation of derived metal complexes and applications in catalysis.

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

5. Organotrifluoroborates and monocoordinated palladium complexes as catalysts--a perfect combination for Suzuki-Miyaura coupling.

6. Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods.

7. A proposed simulation method for directed self-assembly of nanographene.

8. Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling.

9. Synthesis of 3-aryl-1-phosphinoimidazo[1,5-a]pyridine ligands for use in Suzuki-Miyaura cross-coupling reactions.

10. Ylide-Functionalized Phosphines: Strong Donor Ligands for Homogeneous Catalysis.