New Efficient Procedures for Direct Introduction of the Agrochemically Important β-Methoxypropenoate Unit into Substituted Aromatic Derivatives

Synlett

Volumn 1996, Issue 4, 1996, Pages 356-358

  Rossi, Renzo ^a   Bellina, Fabio ^a   Carpita, Adriano ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001851313     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5403     Document Type: Article

References (22)

1. Clough, J. M. Nat. Prod. Rep. 1993, 10, 565.
2. Clough, J. M.; Godfrey, C. R. A. Chemistry in Britain 1995, 466.
3. (a) Hodgson, D. M.; Witherington, J.; Moloney, B. A.; Richards, I. C.; Brayer, J.-L. Synlett 1995, 32;
4. (b) Brayer, J.-L.; Hodgson, D. M.; Richards, I. C.; Witherington, J. PCT Appl. WO 94 24,085; Chem. Abstr. 1995, 122, 265031e.
5. 3: C, 24.81; H, 2.91. Found: C, 24.95; H, 3.01.
6. 2 in THF at 0°C.
7. Rossi, R.; Bellina, F.; Carpita, A.; Gori, R. Synlett 1995, 344.
8. Bellina, F.; Carpita, A.; De Santis, M.; Rossi, R. Tetrahedron Lett. 1994, 35, 6913.
9. Rossi, R.; Bellina, F.; Carpita, A.; Gori, R. Gazz. Chim. Ital. 1995, 125, 381.
10. For previously reported Pd-catalyzed carbon-sulfur bond forming reactions involving alkenyl halides, see: (a) Murahashi, S.; Yamamura, M.; Yanagisawa, K.; Mita, N.; Kondo, K. J. Org. Chem. 1979, 44, 2408; (b) Carpita, A.; Rossi, R., Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. For general aspects of carbon-heteroatom bond forming reactions, see: Barafiano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937 and references cited therein.
11. For previously reported Pd-catalyzed carbon-sulfur bond forming reactions involving alkenyl halides, see: (a) Murahashi, S.; Yamamura, M.; Yanagisawa, K.; Mita, N.; Kondo, K. J. Org. Chem. 1979, 44, 2408; (b) Carpita, A.; Rossi, R., Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. For general aspects of carbon-heteroatom bond forming reactions, see: Barafiano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937 and references cited therein.
12. For previously reported Pd-catalyzed carbon-sulfur bond forming reactions involving alkenyl halides, see: (a) Murahashi, S.; Yamamura, M.; Yanagisawa, K.; Mita, N.; Kondo, K. J. Org. Chem. 1979, 44, 2408; (b) Carpita, A.; Rossi, R., Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. For general aspects of carbon-heteroatom bond forming reactions, see: Barafiano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937 and references cited therein.
13. 3: C, 30.80; H, 3.62. Found: C, 30.52; H, 3.44.
14. For a synthesis of a stereoisomeric mixture of 6 (E : Z = 1 : 1), see: Paliichuk, Y. A.; Kozhushko, B. N.; Shokol, V. A. J. Gen. Chem USSR 1989, 59, 264; Chem Abstr. 1989, 111, 134331.
15. For a synthesis of a stereoisomeric mixture of 6 (E : Z = 1 : 1), see: Paliichuk, Y. A.; Kozhushko, B. N.; Shokol, V. A. J. Gen. Chem USSR 1989, 59, 264; Chem Abstr. 1989, 111, 134331.
16. Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905.
17. A similar procedure has been used to prepare (Z)-1-acetoxy-1,2-diaryethenes from arylboronic acids and (Z)-1-bromo-2-acetoxy-2-arylethenes: Abe, S.; Miyaura, N.; Suzuki, A. Bull. Chem. Soc. Jpn. 1992, 65, 2863.
18. This compound was commercially available.
19. Chan, K.S.; Zhou, X.; Au, M.T.; Tam, C.Y. Tetrahedron 1995, 51, 3129.
20. Diorazio, L.J.; Widdowson, D.A.; Clough, J.M. Tetrahedron 1992, 48, 8073.
21. 3, 4,4′-dichlorobiphenyl was the main reaction product.
22. This compound was prepared according to the general procedure reported in Ref. 15.