Literature DB >> 12375998

Ru3(CO)12-catalyzed C-H/CO/olefin coupling of N-pyridylindolines. Direct carbonylation at a C-H bond delta to the pyridine nitrogen.

Naoto Chatani1, Shuhei Yorimitsu, Taku Asaumi, Fumitoshi Kakiuchi, Shinji Murai.   

Abstract

The reaction of N-pyridylindolines with CO and ethylene in the presence of Ru3(CO)12 results in direct carbonylation at a C-H bond delta to the pyridine sp2 nitrogen, which represents a new type of C-H/CO/olefin coupling. The presence of a pyridine ring as a directing group on the substrates is essential for the reaction to proceed. The choice of N,N-dimethylacetamide (DMA) as the solvent is crucial for the reaction to proceed efficiently.

Entities:  

Year:  2002        PMID: 12375998     DOI: 10.1021/jo0259865

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


  3 in total

Review 1.  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

Review 2.  A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors:  Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal:  Chem Soc Rev       Date:  2018-08-28       Impact factor: 54.564

3.  Rhodium-Catalyzed C(sp2)-H Alkoxycarbonylation/Acylation of Indolines with Anhydrides as a Carbonyl Source.

Authors:  Hirotsugu Suzuki; Fumito Sasamori; Takanori Matsuda
Journal:  Org Lett       Date:  2022-01-31       Impact factor: 6.005

  3 in total

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