Literature DB >> 12688760

Double-chelation-assisted Rh-catalyzed intermolecular hydroacylation.

Masakazu Tanaka1, Masanori Imai, Yoichiro Yamamoto, Keitaro Tanaka, Masato Shimowatari, Shinji Nagumo, Norio Kawahara, Hiroshi Suemune.   

Abstract

[reaction: see text] Rh-Catalyzed intermolecular hydroacylation between salicylaldehydes and 1,5-hexadienes proceeded under remarkably mild reaction conditions to afford a mixture of iso- and normal-hydroacylated products in good yields. The experiments using deuterated salicylaldehyde-d revealed that "double chelation" of salicylaldehyde and 1,5-hexadiene to Rh-complex played vital roles in the catalytic cycle of intermolecular hydroacylation.

Entities:  

Year:  2003        PMID： 12688760     DOI： 10.1021/ol034343o

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


  7 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

Review 4.  Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.

Authors:  Denise A Colby; Robert G Bergman; Jonathan A Ellman
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

5.  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

6.  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

7.  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
  7 in total

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