Trifluoromethylated internal alkynes: Versatile building blocks for the preparation of various fluorine-containing molecules

Synlett

Volumn 25, Issue 10, 2014, Pages 1350-1370

  Konno, Tsutomu ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

bismetallation; carbometallation; cyclization; hydrometallation; regioselectivity; stereoselectivity; trifluoromethylated alkynes

Indexed keywords

ALKYNE; TRIFLUOROMETHYLATED ALKYNE DERIVATIVE; TRIFLUOROMETHYLATED BENZENE DERIVATIVE; TRIFLUOROMETHYLATED BENZOFURAN DERIVATIVE; TRIFLUOROMETHYLATED CYCLOPENTENONE DERIVATIVE; TRIFLUOROMETHYLATED DIHYDROISOXAZOLE DERIVATIVE; TRIFLUOROMETHYLATED INDOLE DERIVATIVE; TRIFLUOROMETHYLATED ISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; BISSTANNYLATION; CARBOCUPRATION; CARBOPALLADATION; CARBOSTANNYLATION; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CROSS COUPLING REACTION; CYCLIZATION; CYCLOTRIMERIZATION REACTION; HYDROBORATION; HYDROMETALLATION; HYDROSILYLATION; HYDROSTANNATION; MOLECULAR INTERACTION; NICHOLAS REACTION; ONE POT SYNTHESIS; SILYLSTANNYLATION; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84902116217     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0033-1340867     Document Type: Article

References (98)

1. Purser S., Moore P. R., Swallow S., Gouverneur V. Chem. Soc. Rev.: 2008; 37 320
2. Müller K., Faeh C., Diederich F. Science: 2007; 317 1881
3. Isanbor C., O'Hagan D. J. Fluorine Chem.: 2006; 127 303
4. Kirk K. L. J. Fluorine Chem.: 2006; 127 1013
5. Bégué J.-P, Bonnet-Delpon D. J. Fluorine Chem.: 2006; 127 992
6. Paulini R., Müller K., Diederich F. Angew. Chem. Int. Ed.: 2005; 44 1788
7. Zanda M. New J. Chem.: 2004; 28 1401
8. Nie J., Guo H.-C, Cahard D., Ma J.-A. Chem. Rev.: 2011; 111 455
9. Valero G., Companyó X., Rios R. Chem. Eur. J.: 2011; 17 2018
10. Qiu X.-L, Qing F.-L. Eur. J. Org. Chem.: 2011; 3261
11. Shimizu M., Hiyama T. Angew. Chem. Int. Ed.: 2005; 44 214
12. Mikami K., Itoh Y., Yamanaka M. Chem. Rev.: 2004; 104 1
13. Lin P., Jiang J. Tetrahedron: 2000; 56 3635
14. Singh R. P., Shreeve J. M. Tetrahedron: 2000; 56 7613
15. Yamanaka H., Mantani T., Shiomi K., Ishihara T. Chem. Lett.: 1998; 615
16. Yamazaki T., Mizutani K., Kitazume T. J. Org. Chem.: 1995; 60 6046
17. Yamazaki T., Mizutani K., Kitazume T. J. Chem. Soc., Chem. Commun.: 1995; 51
18. Umemoto T., Ishihara S. J. Am. Chem. Soc.: 1993; 115 2156
19. Hamper B. C. Org. Synth.: 1991; 70 246
20. Laurent A. J., Le Drean I. M., Selmi A. Tetrahedron Lett.: 1991; 26 3071
21. Meazza G., Capuzzi L., Piccardi P. Synthesis: 1989; 331
22. Bunch J. E., Bumgardner C. L. J. Fluorine Chem.: 1987; 36 313
23. Baum K., Bedford C. D., Hunadi R. J. J. Org. Chem.: 1982; 47 2251
24. Calas P., Moreau P., Commeyras A. J. Chem. Soc., Chem. Commun.: 1982; 433
25. Kobayashi Y., Yamashita T., Takahashi K., Kuroda H., Kumadaki I. Tetrahedron Lett.: 1982; 23 343
26. Finnegan W. G., Norris W. P. J. Org. Chem.: 1963; 28 1139
27. Hiyama T., Sato K. Synlett: 1990; 53
28. Kuwabara M., Fukunishi K., Nomura M., Yamanaka H. J. Fluorine Chem.: 1988; 41 227
29. Kuwabara M., Murakami A., Fukunishi K., Nomura M., Yamanaka H. J. Fluorine Chem.: 1989; 42 105
30. Xu T., Liu G. Org. Lett.: 2012; 14 5416
31. Hanamoto T., Hakoshima Y., Egashira M. Tetrahedron Lett.: 2004; 45 7573
32. Porta P. L., Capuzzai L., Bettarini F. Synthesis: 1994; 287
33. Meazza G., Zanardi G. J. Fluorine Chem.: 1991; 55 199
34. Zhang X.-G, Chen M.-W, Zhong P., Hu M.-H. J. Fluorine Chem.: 2008; 129 335
35. Prié G., Thibonnet J., Abarbri M., Duchêne A., Parrain J.-L. Synlett: 1998; 839
36. Qing F.-L, Zhang Y. Tetrahedron Lett.: 1997; 38 6729
37. Henne A. L., Nager M. J. Am. Chem. Soc.: 1952; 74 650
38. Prié G., Richard S., Parrain J.-L, Duchêne A., Abarbri M. J. Fluorine Chem.: 2002; 117 35
39. Cen W., Ni Y., Shen Y. J. Fluorine Chem.: 1995; 73 161
40. Tamura K., Ishihara T., Yamanaka H. J. Fluorine Chem.: 1994; 68 25
41. Yamanaka H., Tamura K., Funabiki K., Fukunishi K., Ishihara T. J. Fluorine Chem.: 1992; 57 177
42. Funabiki K., Tamura K., Ishihara T., Yamanaka H. Bull. Chem. Soc. Jpn.: 1994; 67 3021
43. Allen A. D., Angelini G., Paradisi C. Tetrahedron Lett.: 1989; 30 1315
44. Iqbal N., Jung J., Park S., Cho E. J. Angew. Chem. Int. Ed.: 2014; 53 539
45. Wang X., Lin J., Zhang C., Xiao J., Zheng X. Chin. J. Chem.: 2013; 31 915
46. Presset M., Oehlrich D., Rombouts F., Molander G. A. J. Org. Chem.: 2013; 78 12837
47. Zheng H., Huang Y., Wang Z., Li H., Huang K.-W, Yuan Y., Weng Z. Tetrahedron Lett.: 2012; 53 6646
48. Jiang X., Chu L., Qing F.-L. J. Org. Chem.: 2012; 77 1251
49. Luo D.-F, Xu J., Fu Y., Guo Q.-X. Tetrahedron Lett.: 2012; 53 2769
50. Weng Z., Li H., He W., Yao L.-F, Tan J., Chen J., Yuan Y., Huang K.-W. Tetrahedron: 2012; 68 2527
51. Zhang K., Qiu X.-L, Huang Y., Qing F.-L. Eur. J. Org. Chem.: 2012; 58
52. Senecal T. D., Parsons A. T., Buchwald S. L. J. Org. Chem.: 2011; 76 1174
53. Urban C., Cadoret F., Blazejewski J.-C, Magnier E. Eur. J. Org. Chem.: 2011; 4862
54. Chu L., Qing F.-L. J. Am. Chem. Soc.: 2010; 30 3229
55. Chu L., Qing F.-L. Org. Lett.: 2010; 12 5060
56. Chu L., Qing F.-L. J. Am. Chem. Soc.: 2010; 132 7262
57. Chen X.-Y, Qiu X.-L, Qing F.-L. Tetrahedron: 2008; 64 2310
58. Ishihara T., Mantani T., Konno T., Yamanaka H. Tetrahedron: 2006; 62 3783
59. Brisdon A. K., Crossley I. R. Chem. Commun.: 2002; 2420
60. Duda B., Tverdomed S., Röschenthaler G.-V. J. Fluorine Chem.: 2013; 152 29
61. Alkhafaji H. M. H, Ryabukhin D. S., Muzalevskiy V. M., Vasilyev A. V., Fukin G. K., Shastin A. V., Nenajdenko V. G. Eur. J. Org. Chem.: 2013; 1132
62. Matsumoto A., Ilies L., Nakamura E. J. Am. Chem. Soc.: 2011; 133 6557
63. Aikawa K., Hioki Y., Shimizu N., Mikami K. J. Am. Chem. Soc.: 2011; 133 20092
64. Katagiri T., Nakanishi H., Ohno K., Seiki T., Isobe T., Kataoka K., Uneyama K. Tetrahedron: 2011; 67 3041
65. Kawatsura M., Namioka J., Kajita K., Yamamoto M., Tsuji H., Itoh T. Org. Lett.: 2011; 13 3285
66. Lumbroso A., Vautravers N. R., Breit B. Org. Lett.: 2010; 12 5498
67. Hanamoto T., Yamada K. J. Org. Chem.: 2009; 74 7559
68. Shimizu M., Higashi M., Takeda Y., Jiang G., Murai M., Hiyama T. Synlett: 2007; 1163
69. Konno T., Ishihara T. In Fluorine-Containing Synthons. Solochonok V. A. American Chemical Society Washington DC: 2005; Chap. 9, 190-203
70. Labrosse J.-R, Lhoste P., Sinou D. J. Org. Chem.: 2001; 66 6634
71. Konno T., Moriyasu K., Ishihara T. Synthesis: 2009; 1087
72. Chen X.-Y, Qiu X.-L, Qing F.-L. Tetrahedron: 2008; 64 2301
73. Chen Q., Qiu X.-L, Qing F.-L. J. Fluorine Chem.: 2007; 128 1182
74. Konno T., Chae J., Tanaka T., Ishihara T., Yamanaka H. J. Fluorine Chem.: 2006; 127 36
75. Chae J., Konno T., Kanda M., Ishihara T., Yamanaka H. J. Fluorine Chem.: 2003; 120 185
76. Konno T., Takehana T., Chae J., Ishihara T., Yamanaka H. J. Org. Chem.: 2004; 69 2188
77. Shimizu M., Jiang G., Murai M., Takeda Y., Nakao Y., Hiyama T., Shirakawa E. Chem. Lett.: 2005; 1700
78. Shirakawa E., Yoshida H., Nakao Y., Hiyama T. Org. Lett.: 2000; 2 2209
79. Konno T., Morigaki A., Ninomiya K., Miyabe T., Ishihara T. Synthesis: 2008; 564
80. Konno T., Daitoh T., Noiri A., Chae J., Ishihara T., Yamanaka H. Tetrahedron: 2005; 61 9391
81. Konno T., Daitoh T., Noiri A., Chae J., Ishihara T., Yamanaka H. Org. Lett.: 2004; 6 933
82. Konno T., Chae J., Ishihara T., Yamanaka H. J. Org. Chem.: 2004; 69 8258
83. Chae J., Konno T., Ishihara T., Yamanaka H. Chem. Lett.: 2004; 33 314
84. Okano T., Matsubara H., Kusukawa T., Fujita M. J. Organomet. Chem.: 2003; 676 43
85. Konno T., Nagata K., Ishihara T., Yamanaka H. J. Org. Chem.: 2002; 67 1768
86. Konno T., Ishihara T., Yamanaka H. Tetrahedron Lett.: 2000; 41 8467
87. Hanzawa Y., Ishizawa S., Ito H., Kobayashi Y., Taguchi T. J. Chem. Soc., Chem. Commun.: 1990; 394
88. Hanzawa Y., Ishizawa S., Kobayashi Y. Chem. Pharm. Bull.: 1988; 36 4209
89. Hirakawa T., Kawatsura M., Itoh T. J. Fluorine Chem.: 2013; 152 62
90. Hirakawa T., Ikeda K., Ikeda D., Tanaka T., Ogasa H., Kawatsura M., Itoh T. Tetrahedron: 2011; 43 8238
91. Larock R. C., Yum E. K., Refvik M. D. J. Org. Chem.: 1998; 63 7652
92. Larock R. C., Yum E. K., Doty M. J., Sham K. K. C. J. Org. Chem.: 1995; 60 3270
93. Bumgardner C. L., Bunch J. E., Whangbo M.-H. J. Org. Chem.: 1986; 51 4083
94. Bunch J. E., Whangbo M.-H. Tetrahedron Lett.: 1986; 27 1883
95. Müller C., Lachicotte R. J., Jones W. D. Organometallics: 2002; 21 1975
96. Garcia J. J., Sierra C., Torrens H. Tetrahedron Lett.: 1996; 37 6097
97. Konno T., Moriyasu K., Kinugawa R., Ishihara T. Org. Biomol. Chem.: 2010; 8 1718
98. Kawatsura M., Yamamoto M., Namioka J., Kajita K., Hirakawa T., Itoh T. Org. Lett.: 2011; 13 1001