Synthesis of allyl acetates via palladium-catalysed functionalisation of allenes and 1,3-dienes

Synthesis

Volumn 44, Issue 3, 2012, Pages 399-408

  Husinec, Suren ^a   Petkovic, Milos ^b   Savic, Vladimir ^b   Simic, Milena ^b  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

allenes; allyl acetates; dienes; palladium catalysis; synthesis

Indexed keywords

1 ,3-DIENES; ALLENES; ALLYL ACETATE; ARYL IODIDES; CATALYTIC SYSTEM; COMPLEX COMPOUNDS; DIENES; FUNCTIONALISATION; GOOD YIELD; PALLADIUM CATALYSIS; SODIUM ACETATE;

CATALYSIS; OLEFINS; SODIUM; SYNTHESIS (CHEMICAL);

ORGANOMETALLICS;

1 (BENZYLOXY) 3 (2 NITROPHENYL)BUT 3 EN 2 YL ACETIC ACID; 1 (BENZYLOXY) 3 (3 METHOXYPHENYL)BUT 3 EN 2 YL ACETIC ACID; 1 (BENZYLOXY) 3 (3,4 DIMETHYLPHENYL)BUT 3 EN 2 YL ACETIC ACID; 1 (BENZYLOXY) 3 (NAPHTHALEN 1 YL)BUT 3 EN 2 YL ACETIC ACID; 1 (BENZYLOXY) 3 4 TOLYLBUT 3 EN 2 YL ACETIC ACID; 1 (BENZYLOXY) 3 PHENYLBUT 3 EN 2 YL ACETIC ACID; 1 [BENZYL(TOSYL)AMINO] 2 (4 METHOXYPHENYL)ALLYL ACETIC ACID; 1,3 DIENE DERIVATIVE; 2 (4 ACETYLPHENYL) 4 (BENZYLOXY)BUT 2 ENYL ACETIC ACID; 2 [2 [BENZYL(TOSYL)AMINO]ETHYLIDENE] 3 (METHOXYMETHYL)BUT 3 ENYL ACETIC ACID; 3 (4 ACETYLPHENYL) 1 (BENZYLOXY)BUT 3 EN 2 YL ACETIC ACID; 3 [BENZYL(TOSYL)AMINO] 2 (4 METHOXYPHENYL)ALLYL ACETIC ACID; 4 (BENZYLOXY) 2 (2 NITROPHENYL)BUT 2 ENYL ACETIC ACID; 4 (BENZYLOXY) 2 (3 METHOXYPHENYL)BUT 2 ENYL ACETIC ACID; 4 (BENZYLOXY) 2 (3,4 DIMETHYLPHENYL)BUT 2 ENYL ACETIC ACID; 4 (BENZYLOXY) 2 (NAPHTHALEN 1 YL)BUT 2 ENYL ACETIC ACID; 4 (BENZYLOXY) 2 4 TOLYLBUT 2 ENYL ACETIC ACID; 4 (BENZYLOXY) 2 PHENYLBUT 2 ENYL ACETIC ACID; 4 [BENZYL(TOSYL)AMINO] 2 (4 METHOXYPHENYL)BUT 2 ENYL ACETIC ACID; 4 [BENZYL(TOSYL)AMINO] 2 4 TOLYLBUT 2 ENYL ACETIC ACID; 4 [BENZYL(TOSYL)AMINO] 2 PHENYLBUT 2 ENYL ACETIC ACID; ACETIC ACID DERIVATIVE; ALLENE DERIVATIVE; N (BUTA 2,3 DIENYL) 2 IODO N TOSYLBENZENAMINE; N BENZYL N TOSYLBUTA 2,3 DIEN 1 AMINE; N MESYL N (PROPA 1,2 DIENYL)BENZENAMINE; PALLADIUM; PALLADIUM ACETATE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ANALYTIC METHOD; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; NUCLEOPHILICITY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84856231784     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289658     Document Type: Article

References (50)

1. Lu Z, Ma S, Angew. Chem. Int. Ed. 2008 47 258
2. Hyland C, Tetrahedron 2005 61 3457
3. Trost B M., Crawley M L., Chem. Rev. 2003 103 2921
4. He J, Tang S, Tang S, Liu J, Sun Y, Pan X, She X, Tetrahedron Lett. 2009 50 430
5. Lebeuf R, Hirano K, Glorius F, Org. Lett. 2008 10 4243
6. Kim I S., Han S B., Krische M J., J. Am. Chem. Soc. 2009 131 2514
7. Denmark S E., Nguyen S T., Org. Lett. 2009 11 781
8. Gan K.-H, Jhong C.-J, Shue Y.-J, Yang S.-C, Tetrahedron 2008 64 9625
9. Kawatsura M, Ata F, Hirakawa T, Hayase S, Itoh T, Tetrahedron Lett. 2008 49 4873
10. Chai Y, Hong S, Lindsay H A., McFarland C, Mcintosh M C., Tetrahedron 2002 58 2905
11. Pereira S, Srebnik M, Aldrichimica Acta 1993 26 17
12. For a recent review on allyl alcohol preparation, see:, Hodgson D M., Humphreys P G., In Science of Synthesis Vol. 36 Clayden J P. Georg Thieme Verlag Stuttgart 2007 583
13. Serra-Muns A, Guerinot A, Reymond S, Cossy J, Chem. Commun. 2010 46 4178
14. Ueda M, Kawai S, Hayashi M, Naito T, Miyata O, J. Org. Chem. 2010 75 914
15. Jimenez-Nunez E, Claverie C K., Bour C, Cardenas D J., Echavarren A M., Angew. Chem. Int. Ed. 2008 47 7892
16. Marion N, Gealageas R, Nolan S P., Org. Lett. 2007 9 2653
17. For some recent examples, see:, Jiang M, Wei Y, Shi M, J. Org. Chem. 2010 75 2528
18. Henderson W H., Check C T., Proust N, Stambuli J P., Org. Lett. 2010 12 824
19. Sheng S.-R, Huang X, J. Chem. Res., Synop. 2002 184
20. Pilarski L T., Selander N, Boese D, Szabo K J., Org. Lett. 2009 11 5518
21. Covell D J., White M C., Angew. Chem. Int. Ed. 2008 47 6448
22. Chen M S., Prabagaran N, Labenz N A., White M C., J. Am. Chem. Soc. 2005 127 6970
23. Grennberg H, Bckvall J E., Chem. Eur. J. 1998 4 1083
24. Yang H, Khan M A., Nicholas K M., [nl]J. Mol. Catal. 1994 91 319
25. Su Y, Jiao N, Org. Lett. 2009 11 2980
26. Bckvall J E., Schink H E., Renko Z D., J. Org. Chem. 1990 55 826; and references cited therein
27. Husinec S, Jadranin M, Markovic R, Petkovic M, Savic V, Todorovic N, Tetrahedron Lett. 2010 51 4066
28. Li Q, Jiang X, Fu C, Ma S, Org. Lett. 2011 13 466
29. Shu W, Yu Q, Ma S, Adv. Synth. Catal. 2009 351 2807
30. Bi H.-P, Liu X.-Y, Gou F.-R, Guo L.-N, Duan X.-H, Liang Y.-M, Org. Lett. 2007 9 3527
31. Dondas H A., Clique B, Cetinkaya B, Grigg R, Kilner C, Morris J, Sridharan V, Tetrahedron 2005 61 10652
32. Larock R C., Wang Y, Dong X, Yao T, Tetrahedron 2005 61 11427
33. VanLaren M W., Diederen J J. H., Elsevier C J., Adv. Synth. Catal. 2001 343 255
34. Zimmer R, Dinesh C U., Nandanan E, Khan F A., Chem. Rev. 2000 100 3067
35. Rutjes F P. J. T., Tjen K C. M. F., Wolf L B., Karstens W F. J., Schoemaker H E., Hiemstra H, Org. Lett. 1999 1 717
36. Anzai M, Toda A, Ohno H, Takemoto Y, Fujii N, Ibuka T, Tetrahedron Lett. 1999 40 7393
37. Shimizu I, Tsuji J, Chem. Lett. 1984 233
38. Shin C, Oh Y, Cha J H., Pae A N., Choo H, Cho Y S., Tetrahedron 2007 63 2182
39. Chakmavarty M, Swamy K C. K., J. Org. Chem. 2006 71 9128
40. Zenner J M., Larock R C., J. Org. Chem. 1999 64 7312
41. Larock R C., He Y, Leong W W., Han X, Refvik M D., Zenner J M., J. Org. Chem. 1998 63 2154
42. Norsikian S, Chang C.-W, Curr. Org. Synth. 2009 6 264; and references cited therein
43. Grigg R, Sridharan V, Xu L.-H, J. Chem. Soc., Chem. Commun. 1995 1903
44. Nakamura H, Sugiishi T, Tanaka Y, Tetrahedron Lett. 2008 49 7230
45. Inamoto K, Yamamoto A, Ohsawa K, Hiroya K, Sakamoto T, Chem. Pharm. Bull. 2005 53 1502
46. Fuwa H, Sasaki M, Org. Biomol. Chem. 2007 5 2214
47. Grigg R, Sansano J M., Santhakumar V, Sridharan V, Thangavelanthum R, Thornton-Pett M, Wilson D, Tetrahedron 1997 53 11803
48. Grigg R, Sansano J M., Tetrahedron 1996 52 13441
49. Wei L L., Mulder J A., Xiong H, Zificsak C A., Douglas C J., Hsung R P., Tetrahedron 2001 57 459
50. Bhat L, Steinig A, Appelbe R, deMeijere A, Eur. J. Org. Chem. 2001 167