Download PDF
Synlett 1997; 1997(12): 1367-1370
DOI: 10.1055/s-1997-1040
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Stereo- and Regioselective Palladium-Catalysed Hydroarylation and Hydrovinylation of Functionalised Alkynes: a Route to Substituted Z-2-Cinnamyl Esters, 3-Chromen-2-ols, and Coumarins

Sandro Cacchi* , Giancarlo Fabrizi, Leonardo Moro, Paola Pace
  • *Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università “La Sapienza”, P.le A. Moro 5, 00185 Roma, Italy, Fax: +39 (6) 4991.2780; e-mail: cacchi@axrma.uniroma1.it
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

The palladium-catalysed hydroarylation and hydrovinylation of methyl 3-phenylpropynoate and 3,3-diethyoxy-1-(o-tetrahydropyranyloxy)phenyl-1-propyne with aryl and vinyl halides or triflates in the presence of Pd(OAc)2 and KOOCH has been studied. The reaction affords stereoselectively syn addition products. The regiochemical outcome appears to be controlled by steric effects and the new carbon-carbon bond is generated preferentially on the carbon far from the aromatic ring ligated to the acetylenic carbon. The reaction can be applied to the synthesis of 3-substituted-3-chromen-2-ols and 3-substituted coumarins.

palladium - hydroarylation - hydrovinylation - cyclization - cinnamyl esters - chromenols - coumarins