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Synlett 1997; 1997(12): 1367-1370
DOI: 10.1055/s-1997-1040
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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
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Publication Date:
31 December 2000 (online)

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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

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