Ligand-free copper-catalyzed arylation of olefins by the mizoroki-heck reaction

Synthesis

Volumn , Issue 2, 2011, Pages 213-216

  Peng, Yong ^a   Chen, Jiuxi ^a   Ding, Jinchang ^a,b   Liu, Miaochang ^a   Gao, Wenxia ^a   Wu, Huayue ^a  

^a WENZHOU UNIVERSITY   (China)

^b WENZHOU VOCATIONAL AND TECHNICAL COLLEGE   (China)

Author keywords

copper catalyzed; cross coupling; E internal olefins; ligand free; Mizoroki Heck reaction

Indexed keywords

ARYL IODIDES; ARYLATIONS; CROSS-COUPLINGS; E-INTERNAL OLEFINS; GOOD YIELD; HECK CROSS-COUPLING REACTION; LIGAND-FREE; MIZOROKI-HECK REACTION; NOVEL LIGANDS; OPTIMAL SOLVENTS; TETRAMETHYLAMMONIUM;

BROMINE COMPOUNDS; CATALYSIS; COPPER; LIGANDS; OLEFINS;

REACTION KINETICS;

ALKENE; COPPER; IODOBENZENE; METHYL 2 METHYL 3 (2 NITROPHENYL)ACRYLATE; TETRAMETHYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; HECK REACTION; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 78650867093     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258338     Document Type: Article

References (41)

1. Heck R F., Nollwy J P., J. Org. Chem. 1972 37 2320
2. Mizoroki T, Mori K, Ozaki A, Bull. Chem. Soc. Jpn. 1971 44 581
3. Gaudin J M., Tetrahedron Lett. 1991 32 6113
4. Overman L E., Ricca D J., Tran V D., J. Am. Chem. Soc. 1993 115 2042
5. Tietze L F., Buhr W, Angew. Chem., Int. Ed. Engl. 1995 34 1366
6. Wu X F., Neumann H, Beller M, Angew. Chem. Int. Ed. 2010 49 5284
7. Chapman L M., Adams B, Kliman L T., Makriyannis A, Hamblett C L., Tetrahedron Lett. 2010 51 1517
8. Ren G R., Cui X L., Yang E B., Yang F, Wu Y J., Tetrahedron 2010 66 4022
9. Hajipour R, Karami K, Pirisedigh A, Ruoho A E., J. Organomet. Chem. 2009 694 2548
10. Cui X, Li Z, Tao C Z., Xu Y, Li J, Liu L, Guo Q X., Org. Lett. 2006 8 2467
11. Ohff M, Ohff A, Milstein D, Chem. Commun. 1999 357
12. Bergbreiter E, Osburn P L., Wilson A, Sink E, J. Am. Chem. Soc. 2000 122 9058
13. Herrmann W A., Angew. Chem. Int. Ed. 2002 41 1290
14. Nolan S P., Lee H M., Yang C, Org. Lett. 2001 3 1511
15. Xie G, Chellan P, Mao J, Chibale K, Smith G S., Adv. Synth. Catal. 2010 352 1641
16. Pan D L., Jiao N, Synlett 2010 1577
17. Reetz M T., Westermann E, Angew. Chem. Int. Ed. 2000 39 165
18. de Vries J G., J. Chem. Soc., Dalton Trans. 2006 421
19. Yao Q W., Kinney E P., Yang Z, J. Org. Chem. 2003 68 7528
20. Carrow B P., Hartwig J F., J. Am. Chem. Soc. 2010 132 79
21. de Vries H M., Mulders J M. C. A., Mommers J H. M., Henderickx H J. W., de Vries J G., Org. Lett. 2003 5 3285
22. Palmisano G, Bonrath W, Boffa L, Garella D, Barge A, Cravatto G, Adv. Synth. Catal. 2007 349 2338
23. Boldini G P., Savoia D, Tagliavani E, Trombini C, Ronchi A U., J. Organomet. Chem. 1986 301 C62
24. Lebedev S A., Lopatina V S., Petrov E S., Beletskaya I P., J. Organomet. Chem. 1988 344 253
25. Sustman R, Hopp P, Holl P, Tetrahedron Lett. 1989 30 689
26. Iyer S, J. Organomet. Chem. 1995 490 C27
27. Iyer S, Thakur V V., J. Mol. Catal., A: Chem. 2000 157 275
28. Oi S, Sakai K, Inoue Y, Org. Lett. 2005 7 4009
29. Yorke J, Wan L, Xia A, Zheng W, Tetrahedron Lett. 2007 48 8843
30. Xu L, Chen W, Ros J, Xiao J, Org. Lett. 2001 3 295
31. Zhou L, Wang L, Synthesis 2006 2653
32. Kamal A, Reddy D R., Rajendar, Tetrahedron Lett. 2005 46 7951
33. Pham T P. T., Cho C.-W, Yun Y S., Water Res. 2010 44 352
34. Loska R, Volla C M. R., Vogel P, Adv. Synth. Catal. 2008 350 2859
35. Li J H., Wang D P., Xie Y X., Tetrahedron Lett. 2005 46 4941
36. Cal V, Nacci A, Monopoli A, Ieva E, Cioffi N, Org. Lett. 2005 7 617
37. Declerck V, Martinez J, Lamaty F, Synlett 2006 3029
38. Evano G, Blanchard N, Toumi M, Chem. Rev. 2008 108 3054
39. Kenichi Y, Kiyoshi T, Chem. Rev. 2008 108 2874
40. Daugulis O, Do H.-Q, Shabashov D, Acc. Chem. Res. 2009 42 1074
41. Zheng H M., Zhang Q, Chen J X., Liu M C., Cheng S H., Ding J C., Wu H Y., Su W K., J. Org. Chem. 2009 74 943