Literature DB >> 17341091

Direct intermolecular hydroacylation of N,N-dialkylacrylamides with aldehydes catalyzed by a cationic rhodium(I)/dppb complex.

Ken Tanaka1, Yu Shibata, Takeshi Suda, Yuji Hagiwara, Masao Hirano.   

Abstract

[structure: see text]. A cationic rhodium(I)/dppb complex catalyzed direct intermolecular hydroacylation of N,N-dialkylacrylamides with both aliphatic and aromatic aldehydes has been achieved through the stabilization of acylrhodium intermediates by alkene chelation to rhodium. This method represents a versatile new route to gamma-ketoamides in view of the high atom economy and commercial availability of substrates.

Entities:  

Year:  2007        PMID: 17341091     DOI: 10.1021/ol070153s

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  13 in total

1.  Intermolecular Markovnikov-Selective Hydroacylation of Olefins Catalyzed by a Cationic Ruthenium-Hydride Complex.

Authors:  Junghwa Kim; Chae S Yi
Journal:  ACS Catal       Date:  2016-04-19       Impact factor: 13.084

2.  Hydroacylation of 2-Butyne from the Alcohol or Aldehyde Oxidation Level via Ruthenium Catalyzed C-C Bond Forming Transfer Hydrogenation.

Authors:  Vanessa M Williams; Joyce C Leung; Ryan L Patman; Michael J Krische
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

3.  Enantioselective hydroacylation of olefins with rhodium catalysts.

Authors:  Stephen K Murphy; Vy M Dong
Journal:  Chem Commun (Camb)       Date:  2014-11-18       Impact factor: 6.222

4.  Rhodium(I)-Catalyzed Intermolecular Hydroacylation of α-Keto Amides and Isatins with Non-Chelating Aldehydes.

Authors:  Kevin G M Kou; Lauren E Longobardi; Vy M Dong
Journal:  Adv Synth Catal       Date:  2015-07-14       Impact factor: 5.837

5.  Computational Study of Rh-Catalyzed Carboacylation of Olefins: Ligand-Promoted Rhodacycle Isomerization Enables Regioselective C-C Bond Functionalization of Benzocyclobutenones.

Authors:  Gang Lu; Cheng Fang; Tao Xu; Guangbin Dong; Peng Liu
Journal:  J Am Chem Soc       Date:  2015-06-19       Impact factor: 15.419

6.  Substrate-directed hydroacylation: rhodium-catalyzed coupling of vinylphenols and nonchelating aldehydes.

Authors:  Stephen K Murphy; Achim Bruch; Vy M Dong
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-29       Impact factor: 15.336

7.  Mechanistic insights into hydroacylation with non-chelating aldehydes†Electronic supplementary information (ESI) available: Materials and methods, reaction procedures, characterization data. CCDC 1012849. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc02026jClick here for additional data file.

Authors:  Stephen K Murphy; Achim Bruch; Vy M Dong
Journal:  Chem Sci       Date:  2014-09-22       Impact factor: 9.825

8.  Direct Synthesis of Highly Substituted Pyrroles and Dihydropyrroles Using Linear Selective Hydroacylation Reactions.

Authors:  Manjeet K Majhail; Paul M Ylioja; Michael C Willis
Journal:  Chemistry       Date:  2016-04-23       Impact factor: 5.236

9.  Rh(I)-catalyzed intermolecular hydroacylation: enantioselective cross-coupling of aldehydes and ketoamides.

Authors:  Kevin G M Kou; Diane N Le; Vy M Dong
Journal:  J Am Chem Soc       Date:  2014-06-17       Impact factor: 15.419

10.  Regioselective hydroacylation of 1,3-dienes by cobalt catalysis.

Authors:  Qing-An Chen; Daniel K Kim; Vy M Dong
Journal:  J Am Chem Soc       Date:  2014-03-03       Impact factor: 15.419

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