Cu(OTf)2-catalyzed arylmethylation of terminal alkynes with benzylic alcohols under ligand-, base-, and additive-free reaction conditions

Tetrahedron

Volumn 67, Issue 15, 2011, Pages 2753-2759

  Ren, Kai ^a   Li, Pinhua ^a   Wang, Lei ^a,c   Zhang, Xiuli ^b  

^a HUAIBEI NORMAL UNIVERSITY   (China)

^b ANHUI AGRICULTURAL UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Arylmethylation; Benzylic alcohols; C C bond formation; Cu(OTf)2; Terminal alkynes

Indexed keywords

1 (4 CHLOROPHENYL) 3,3 DIPHENYL 1 PROPYNE; 1 (4 FLUOROPHENYL) 3,3 DIPHENYL 1 PROPYNE; 1 (4 METHYLPHENYL) 3,3 DIPHENYL 1 PROPYNE; 1 (4 TERT BUTYLPHENYL) 3,3 DIPHENYL 1 PROPYNE; 1,1 DI(4 CHLOROPHENYL) 3 PHENYL 1 PROPYNE; 1,3 DIPHENYL 3 (2 CHLOROPHENYL) 1 PROPYNE; 1,3 DIPHENYL 3 (4 BROMOPHENYL) 1 PROPYNE; 1,3 DIPHENYL 3 (4 CHLOROPHENYL) 1 PROPYNE; 1,3 DIPHENYL 3 (4 FLUOROPHENYL) 1 PROPYNE; 1,3 DIPHENYL 3 (4 METHYLPHENYL) 1 PROPYNE; 1,3,3 TRIPHENYL 1 PROPYNE; ALKYNE DERIVATIVE; BASE; BENZYL ALCOHOL; LEWIS ACID; LIGAND; PHENYLACETYLENE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ARYLMETHYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; METHYLATION; PRIORITY JOURNAL;

EID: 79952899316     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.02.050     Document Type: Article

References (46)

1. I. Paterson, R.D. Davies, and R. Marquez Angew. Chem., Int. Ed. 40 2001 603 607
2. M. Toyota, C. Komori, and M. Ihara J. Org. Chem. 65 2000 7110 7113
3. F. Yoshimura, S. Kawata, and M. Hirama Tetrahedron Lett. 40 1999 8281 8285
4. M.W. Miller, and C.R. Johnson J. Org. Chem. 62 1997 1582 1583
5. A. Sakai, T. Aoyama, and T. Shioiri Tetrahedron Lett. 40 1999 4211 4214
6. A.E. Graham, D. McKerrecher, D.H. Davies, and R.J.K. Taylor Tetrahedron Lett. 37 1996 7445 7448
7. J. Lam, H. Breteler, T. Arnason, L. Hansen, Chemistry and Biology of Naturally-Occurring Acetylenes and Related Compounds 1988 Elsevier Amsterdam
8. D.V. Banthorpe S. Patai, Chemistry of Triple-Bonded Functional Groups 1994 Wiley New York, NY 689 737
9. N.J. Long, and C.K. Williams Angew. Chem., Int. Ed. 42 2003 2586 2617
10. G.T. Hwang, H.S. Son, J.K. Ku, and B.H. Kim J. Am. Chem. Soc. 125 2003 11241 11248
11. F.-Q. Bai, X. Zhou, B.-H. Xia, T. Liu, J.-P. Zhang, and H.-X. Zhang J. Organomet. Chem. 694 2009 1848 1860
12. R. Wu, J.S. Schumm, D.L. Pearson, and J.M. Tour J. Org. Chem. 61 1996 6906 6921
13. U.H.F. Bunz Chem. Rev. 100 2000 1605 1644
14. P.J. Stang, F. Diederich, Modern Acetylene Chemistry 1995 VCH Weinheim, Germany
15. S. Patai, Chemistry of Triple-Bonded Functional Groups 1994 Wiley New York, NY
16. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 16 1975 4467 4470
17. K. Sonogashira J. Organomet. Chem. 653 2002 46 49
18. F. Diederich, A. Meijere, Metal-catalyzed Cross-Coupling Reactions 2004 Wiley-VCH New York, NY
19. R.R. Tykwinski Angew. Chem., Int. Ed. 42 2003 1566 1568
20. M. Uemura, H. Yorimitsua, and K. Oshima Tetrahedron 64 2008 1829 1833
21. E.-i. Negishi, and L. Anastasia Chem. Rev. 103 2003 1979 2018
22. I. Perez, J.P. Sestelo, and L.A. Sarandeses J. Am. Chem. Soc. 123 2001 4155 4160
23. I. Perez, J.P. Sestelo, and L.A. Sarandeses Org. Lett. 1 1999 1267 1269
24. J.A. Soderquist, K. Matos, A. Rane, and J. Ramos Tetrahedron Lett. 36 1995 2401 2402
25. A. Furstner, and G. Seidel Tetrahedron 51 1995 11165 11176
26. A.-S. Castanet, F. Colobert, and T. Schlama Org. Lett. 2 2000 3559 3561
27. C.H. Oh, and S.H. Jung Tetrahedron Lett. 41 2000 8513 8516
28. G.A. Molander, B.W. Katona, and F. Machrouhi J. Org. Chem. 67 2002 8416 8423
29. L. Anastasia, and E.-i. Negishi Org. Lett. 3 2001 3111 3113
30. M. Qian, and E.-I. Negishi Tetrahedron Lett. 46 2005 2927 2930
31. H.P. Dang, and G. Linstrumelle Tetrahedron Lett. 1978 191 194
32. E.-I. Negishi, Y. Zhang, F.E. Cederbaum, and M.B. Webb J. Org. Chem. 51 1986 4080 4082
33. L.-M. Yang, L.-F. Huang, and T.-Y. Luh Org. Lett. 6 2004 1461 1463
34. V. Farina, V. Krishnamurthy, and W.J. Scott Org. React. 50 1997 1 652
35. D.-M. Cui, N. Hashimoto, S.-I. Ikeda, and Y. Sato J. Org. Chem. 60 1995 5752 5756
36. E.-i. Negishi Acc. Chem. Res. 15 1982 340 348
37. D. Gelman, D. Tsvelikhovsky, G.A. Molander, and J. Blum J. Org. Chem. 67 2002 6287 6290
38. M. Eckhardt, and G.C. Fu J. Am. Chem. Soc. 125 2003 13642 13643
39. G.W. Kabalka, M.L. Yao, and S. Borella Org. Lett. 8 2006 879 881 and references cited therein
40. K.L. Chang, B.L. Wei, and J.B. Wang Tetrahedron Lett. 50 2009 2533 2535
41. B.M. Trost Science 254 1991 1471 1477
42. Z.-Q. Liu, J. Wang, J. Han, Y. Zhao, and B. Zhou Tetrahedron Lett. 50 2009 1240 1242
43. S. Biswas, S. Maiti, and U. Jana Eur. J. Org. Chem. 2009 2354 2359
44. During the preparation of our manuscript, Jiao and co-workers reported the same reaction, they reported that Fe(OTf)3/TfOH co-catalyzed coupling reaction of terminal alkynes with benzylic alcohols, and the highest yield (77%) was reached co-catalyzed by Fe(OTf)3 (5 mol %) and TfOH (10 mol %) in DCE. Markedly, even when 2 mol % of Fe(OTf)3 and 5 mol % of TfOH were employed, the coupling went well giving 70% yield. See: S.K. Xiang, L.H. Zhang, and N. Jiao Chem. Commun. 2009 6487 6489 for detail
45. H. Huang, H.L. Jiang, K.X. Chen, and H. Liu J. Org. Chem. 74 2009 5476 5480
46. K. Ren, M. Wang, and L. Wang Eur. J. Org. Chem. 2010 565 571