Literature DB >> 21895010

A homogeneous, recyclable polymer support for Rh(I)-catalyzed C-C bond formation.

Ranjan Jana1, Jon A Tunge.   

Abstract

A robust and practical polymer-supported, homogeneous, recyclable biphephos rhodium(I) catalyst has been developed for C-C bond formation reactions. Control of polymer molecular weight allowed tuning of the polymer solubility such that the polymer-supported catalyst is soluble in nonpolar solvents and insoluble in polar solvents. Using the supported rhodium catalysts, addition of aryl and vinylboronic acids to the electrophiles such as enones, aldehydes, N-sulfonyl aldimines, and alkynes occurs smoothly to provide products in high yields. Additions of terminal alkynes to enones and industrially relevant hydroformylation reactions have also been successfully carried out. Studies show that the leaching of Rh from the polymer support is low and catalyst recycle can be achieved by simple precipitation and filtration.

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Year:  2011        PMID: 21895010      PMCID: PMC3215106          DOI: 10.1021/jo201476h

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


  42 in total

1.  Chiral pi-Allylpalladium-Catalyzed Asymmetric Allylation of Imines: Replacement of Allylstannanes by Allylsilanes.

Authors:  Kaori Nakamura; Hiroyuki Nakamura; Yoshinori Yamamoto
Journal:  J Org Chem       Date:  1999-04-16       Impact factor: 4.354

2.  Catalyzed Asymmetric Arylation Reactions.

Authors:  Carsten Bolm; Jens P. Hildebrand; Kilian Muñiz; Nina Hermanns
Journal:  Angew Chem Int Ed Engl       Date:  2001-09-17       Impact factor: 15.336

3.  Preparation of polymer-supported ligands and metal complexes for use in catalysis.

Authors:  Nicholas E Leadbeater; Maria Marco
Journal:  Chem Rev       Date:  2002-10       Impact factor: 60.622

4.  Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds.

Authors:  Keith Fagnou; Mark Lautens
Journal:  Chem Rev       Date:  2003-01       Impact factor: 60.622

Review 5.  The use of ultra- and nanofiltration techniques in homogeneous catalyst recycling.

Authors:  Harm P Dijkstra; Gerard P M van Klink; Gerard van Koten
Journal:  Acc Chem Res       Date:  2002-09       Impact factor: 22.384

6.  [Formation of pyrroles from gamma-acetylene ketones].

Authors:  J Reisch
Journal:  Arch Pharm Ber Dtsch Pharm Ges       Date:  1965-09

7.  Practical asymmetric synthesis of a potent Cathepsin K inhibitor. Efficient palladium removal following Suzuki coupling.

Authors:  Cheng-Yi Chen; Philippe Dagneau; Edward J J Grabowski; Renata Oballa; Paul O'Shea; Peppi Prasit; Joël Robichaud; Rich Tillyer; Xin Wang
Journal:  J Org Chem       Date:  2003-04-04       Impact factor: 4.354

8.  Rhodium-catalyzed regio- and stereoselective codimerization of alkenes and electron-deficient internal alkynes leading to 1,3-dienes.

Authors:  Yu Shibata; Masao Hirano; Ken Tanaka
Journal:  Org Lett       Date:  2008-06-11       Impact factor: 6.005

9.  A Pauson-Khand-type reaction between alkynes and olefinic aldehydes catalyzed by rhodium/cobalt heterobimetallic nanoparticles: an olefinic aldehyde as an olefin and CO source.

Authors:  Kang Hyun Park; Il Gu Jung; Young Keun Chung
Journal:  Org Lett       Date:  2004-04-01       Impact factor: 6.005

10.  A homogeneous, recyclable rhodium(I) catalyst for the hydroarylation of Michael acceptors.

Authors:  Ranjan Jana; Jon A Tunge
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

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  2 in total

1.  Ir(COD)Cl]2/Tris(2,4-di-t-butylphenyl)phosphite-Catalyzed Addition Reactions of Arylboronic Acids with Aldehydes.

Authors:  Yuan-Xi Liao; Jie Dong; Qiao-Sheng Hu
Journal:  Tetrahedron Lett       Date:  2018-03-02       Impact factor: 2.415

2.  Rh-catalyzed highly regioselective hydroformylation to linear aldehydes by employing porous organic polymer as a ligand.

Authors:  Zhaozhan Wang; Yong Yang
Journal:  RSC Adv       Date:  2020-08-07       Impact factor: 4.036

  2 in total

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