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

Synlett

Volumn , Issue 12, 1997, Pages 1367-1370

  Cacchi, Sandro ^a   Fabrizi, Giancarlo ^a   Moro, Leonardo ^a   Pace, Paola ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002713281     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1040     Document Type: Article

References (23)

1. Cacchi, S. Pure & Appl. Chem. 1990, 62, 713.
2. Arcadi, A.; Cacchi, S.; Ianelli, S.; Marinelli, F.; Nardelli, M. Gazz. Chim. It. 1986, 116, 725.
3. Arcadi, A.; Bernocchi, E.; Burini, A.; Cacchi, S.; Marinelli, F.; Pietroni, B. Tetrahedron Lett. 1989, 30, 3465;
4. Arcadi, A.; Bernocchi, E.; Burini, A.; Cacchi, S.; Marinelli, F.; Pietroni, B. Tetrahedron 1988, 44, 481.
5. Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L; Pace, P. Tetrahedron 1996, 52, 10225.
6. 2 : C, 74.98; H, 5.54. Found C, 74.88; H, 5.56.
7. For the hydroarylation of 1a, see the typical procedure for the hydroaylation of 5d (ref. 15).
8. 13C HETCOR studies. Their stereochemistry was assigned on the basis of NOE studies.
9. Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C. J. Org. Chem. 1995, 60, 3270;
10. Maassarani, F.; Pfeffer, M.; Le Borgne, G. Organometallics 1987, 6, 2029;
11. Maassarani, F.; Pfeffer, M.; Le Borgne, G. Organometallics 1987, 6, 2043.
12. Beydoun, N.; Pfeffer, M. Synthesis 1990, 729.
13. Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Synlett 1996, 568.
14. 2O according to the conditions described in ref. 12. Under the same conditions, o-(tetrahydropyranyloxy)phenyl iodide gave a mixture of 1b and 1c. Compound 1c was prepared in 60% yield through the reaction of 1b with dihydropyran according to standard procedures.
15. Haglund, O. Nilsson, M. Synlett 1991, 723.
16. Compounds 5 were prepared according to the conditions described in: Sakamoto, T.; Shiga, F.; Yasuhara, A.; Uchiyama, D.; Kondo, Y.; Yamanaka, H. Synthesis 1992, 746.
17. 4: C, 71.01; H, 7.95. Found C, 71.12; H, 7.97.
18. 5 : C, 72.78; H, 7.82. Found C, 72.63; H, 7.80.
19. The regio- and stereochemistry of 6 (Table 3) was usually assigned on the basis of NOE studies. In cases where clean NOE studies were prevented by the chemical shifts of the vinylic and aromatic protons, the stereochemistry was assumed to be Z on the basis of the likely structural analogy with the other products in the series and with the results obtained in related reactions.
20. 3 : C, 75.56; H, 5.55. Found C, 75.64; H, 5.57.
21. The regio- and stereochemistry of 8a was assigned on the basis of NOE studies.
22. 3: C, 76.17; H, 4.80. Found C, 76.25; H, 4.79.
23. 4 and concentrated under reduced pressure. The residue was purified by chromatography (silica gel, 40 g; n-hexane/ethyl acetate 90/10 v/ v) to give 10a (0.066 g, 40% yield).