Literature DB >> 11942798

CO-transfer carbonylation reactions. A catalytic Pauson-Khand-type reaction of enynes with aldehydes as a source of carbon monoxide.

Tsumoru Morimoto1, Koji Fuji, Ken Tsutsumi, Kiyomi Kakiuchi.   

Abstract

The reaction of enynes with aldehydes in the presence of a catalytic amount of [RhCl(cod)](2)/dppp results in the Pauson-Khand-type reaction without the use of gaseous carbon monoxide to give bicyclic cyclopentenones in high yields (14 examples). Aldehydes serve as a source of carbon monoxide, and their carbonyl moiety is transferred to enynes, resulting in the formation of the carbonylated products. This reaction represents the first example of a CO-transfer carbonylation.

Entities:  

Year:  2002        PMID: 11942798     DOI: 10.1021/ja0126881

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  7 in total

1.  Theoretical studies on the Mo-catalyzed asymmetric intramolecular Pauson-Khand-type [2+2+1] cycloadditions of 3-allyloxy-1-propynylphosphonates.

Authors:  Qingxi Meng; Ming Li
Journal:  J Mol Model       Date:  2012-08       Impact factor: 1.810

2.  Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene.

Authors:  Alexandre Pradal; Chung-Meng Chao; Patrick Y Toullec; Véronique Michelet
Journal:  Beilstein J Org Chem       Date:  2011-07-26       Impact factor: 2.883

3.  Synthesis of 4H-Benzo[e][1,3]oxazin-4-ones by a Carbonylation-Cyclization Domino Reaction of ortho-Halophenols and Cyanamide.

Authors:  Linda Åkerbladh; Shiao Y Chow; Luke R Odell; Mats Larhed
Journal:  ChemistryOpen       Date:  2017-08-16       Impact factor: 2.911

4.  Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp3)-H functionalization.

Authors:  Yang Li; Gao-Hui Pan; Ming Hu; Bang Liu; Ren-Jie Song; Jin-Heng Li
Journal:  Chem Sci       Date:  2016-07-21       Impact factor: 9.825

5.  Why intermolecular nitric oxide (NO) transfer? Exploring the factors and mechanistic aspects of NO transfer reaction.

Authors:  Sandip Das; Soumyadip Ray; Tarali Devi; Somnath Ghosh; Sarvesh S Harmalkar; Sunder N Dhuri; Padmabati Mondal; Pankaj Kumar
Journal:  Chem Sci       Date:  2022-01-11       Impact factor: 9.825

6.  The use of silicon-based tethers for the Pauson-Khand reaction.

Authors:  Adrian P Dobbs; Ian J Miller; Sasa Martinović
Journal:  Beilstein J Org Chem       Date:  2007-07-06       Impact factor: 2.883

7.  Total Syntheses of Marrubiin and Related Labdane Diterpene Lactones.

Authors:  Yukari Sakagami; Naoki Kondo; Yuki Sawayama; Hiroyuki Yamakoshi; Seiichi Nakamura
Journal:  Molecules       Date:  2020-04-01       Impact factor: 4.411

  7 in total

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