Irradiation of Imine-Group VI Carbene Complexes in the Presence of Alkynes. 2. Control of Product Distribution

  1. Sampedro, D. 1
  2. Caro, M. 1
  3. Rodríguez, M.A. 1
  4. Campos, P.J. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Journal of Organic Chemistry

ISSN: 0022-3263

Any de publicació: 2005

Volum: 70

Número: 17

Pàgines: 6705-6713

Tipus: Article

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DOI: 10.1021/JO050676I SCOPUS: 2-s2.0-23744466461 WoS: WOS:000231183000020 GOOGLE SCHOLAR

Altres publicacions en: Journal of Organic Chemistry

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Resum

The photoreactivity of iminecarbene complexes in the presence of alkynes has been explored. Up to four different reaction paths are available depending on the alkyne and carbene complex substituents, although in each case only one type of product is isolated. 2H-Pyrrole derivatives are formed mainly from aryl alkynes. When alkyl alkynes are used, the method affords a new type of aza-dendralene product in good yields. Isoquinoline derivatives can also be formed in a two-step one-pot photochemical process when the appropriate substituents are present. Finally, indene derivatives are also available through a benzannulation reaction. To explore the underlying mechanism, we carried out computations using DFT methods. Experimental and theoretical results compare well, which allows control over the reaction and product distribution. © 2005 American Chemical Society.