Alkenylation reactions of heteroarenes by transition-metal catalysts

Synthesis

Volumn , Issue 24, 2010, Pages 4131-4153

  Rossi, Renzo ^a   Bellina, Fabio ^a   Lessi, Marco ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

catalysis; coupling; heteroarenes; olefination; transition metals

Indexed keywords

ALKENYL; ALKENYLATION; CARBON-CARBON DOUBLE BONDS; DICARBONYL COMPOUNDS; H-BONDS; HETEROARENES; MIZOROKI-HECK REACTION; OLEFINATION; OPERATIONAL COSTS; ORGANOMETALLIC REAGENT; OXIDATIVE COUPLING REACTIONS; PSEUDO HALIDE; TRANSITION METAL CATALYSTS; TRANSITION-METAL-CATALYZED REACTIONS; TRIFLATES;

ACETYLENE; CATALYSIS; CATALYSTS; OLEFINS; ORGANOMETALLICS;

TRANSITION METALS;

1,3 DICARBONYL; 2 CYANOFURAN; 2 CYANOPYRIDINE; 2 CYANOTHIOPHENE; ACROLEIN; ALKENE DERIVATIVE; ALKENYL GROUP; ALKYNE DERIVATIVE; BENZOFURAN DERIVATIVE; BENZOQUINONE DERIVATIVE; BENZOTHIOPHENE DERIVATIVE; BENZOTRIAZOLE DERIVATIVE; CESIUM; CUPROUS ION; CYANIDE; HALIDE; HETEROARENE DERIVATIVE; IMIDAZOLE DERIVATIVE; N METHYLPYRIMIDONE; PALLADIUM ACETATE; PHOSPHATE; PYRAZOLE DERIVATIVE; PYRIDAZINE DERIVATIVE; PYRIMIDINONE DERIVATIVE; PYRROLE DERIVATIVE; PYRROLIDINE DERIVATIVE; QUINOXALINE DERIVATIVE; TETRAZOLE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ADDITION REACTION; ALKENYLATION; ARYLATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CYANATION; CYCLIZATION; HECK REACTION; HYDROGEN BOND; HYDROLYSIS; OLEFINATION; OLIGOMERIZATION; PHASE TRANSITION; REVIEW; STEREOCHEMISTRY; STILLE REACTION; SYNTHESIS;

EID: 78650172301     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258262     Document Type: Review

References (273)

1. For representative examples, see:, Bishara A, Rudi A, Aknin M, Neimann D, Ben-Califa N, Kashman Y, Org. Lett. 2008 10 4307
2. Yong K W. L., Hooper J N. A., Garson M J., ARKIVOC 2008 (vi) 100
3. Guella G, Ndiaye I, Fofana M, Mancini I, Tetrahedron 2006 62 1165
4. Srinivas P V., Anubala S, Sarma V U. M., Sastry B V. S., Rao J M., J. Planar Chromatogr. 2007 20 73
5. Nett M, Erol, Kehraus S, Köck M, Krick A, Eguereva E, Neu E, König G M., Angew. Chem. Int. Ed. 2006 45 3863
6. Endo T, Tsuda M, Okada T, Mitsuhashi S, Shima H, Kikuchi K, Mikami Y, Fromont J, Kobayashi J, J. Nat. Prod. 2004 67 1262
7. Liu Y, Mansoor T A., Hong J, Lee C.-O, Sim C J., Im K S., Kim N D., Jung J H., J. Nat. Prod. 2003 66 1451
8. Lo S, Zificsak C A., Hsung R P., Org. Lett. 2003 5 4709
9. Eisenbarth S, Steffan B, Tetrahedron 2000 56 363
10. Guo Y W., Trivellone E, Chin. Chem. Lett. 2000 11 327
11. Böhlendorf B, Herrmann M, Hecht H.-J, Sasse F, Forche E, Kunze B, Reichenbach H, Höfle G, Eur. J. Org. Chem. 1999 2601
12. For representative examples, see:, Blanchard S, William A D., Lee A C.-H, Poulsen A, Teo E L., Deng W, Tu N, Tan E, Goh K L., Ong W C., Ng C P., Goh K C., Bonday Z, Sun E T., Bioorg. Med. Chem. Lett. 2010 20 2443
13. Reddy P P., Lavekar A G., Babu K S., Rao R R., Shasidhar J, Shashikiran G, Rao J M., Bioorg. Med. Chem. Lett. 2010 20 2525
14. Gomez L, Hack M D., McClure K, Schon C, Huang L, Morton M, Li L, Barrett T D., Shankley N, Breitenbucher J G., Bioorg. Med. Chem. Lett. 2007 17 6493
15. Vinsova J, Cermakova K, Tomeckova A, Ceckova M, Jampilek J, Cermak P, Kunes J, Dolezal M, Staud F, Bioorg. Med. Chem. 2006 14 5850
16. Rida S M., Ashour F A., El-Hawash S A. M., ElSemary M M., Badr M H., Shalaby M A., Eur. J. Med. Chem. 2005 40 949
17. Fakhfakh M A., Fournet A, Prina E, Mouscadet J.-F, Franck X, Hocquemiller R, Figadère B, Bioorg. Med. Chem. 2003 11 5013
18. Conde J J., McGuire M, Wallace M, Tetrahedron Lett. 2003 44 3081
19. Repic O, Prasad K, Lee G T., Org. Process Res. Dev. 2001 5 519
20. Shen W, Fakhoury S, Donner G, Henry K, Lee J, Zhang H, Cohen J, Warner R, Saced B, Cherian S, Tahir S, Kovar P, Bauch J, Ng S.-C, Marsh K, Sham H, Rosenberg S, Bioorg. Med. Chem. Lett. 1999 703
21. Paulose B M. J. S., Rayabarapu D K., Duan J.-P, Cheng C.-H, Adv. Mater. (Weinheim, Ger.) 2004 16 2003
22. Velusamy M, Hsu Y.-C, Lin J T., Chang C.-W, Hsu C.-P, Chem. Asian J. 2009 5 87
23. For representative examples, see
24. Bergonzini G, Gramigna L, Mazzanti A, Fochi M, Bernardi L, Ricci A, Chem. Commun. 2010 46 327
25. Rupnicki L, Saxena A, Lam H W., J. Am. Chem. Soc. 2009 131 10386
26. Hoffman T J., Rigby J H., Arseniyadis S, Cossy J, J. Org. Chem. 2008 73 2400
27. Movassaghi M, Ondrus A E., Org. Lett. 2005 7 4423
28. Padwa A, Lynch S M., Oneto J M., Zhang H, J. Org. Chem. 2005 70 2206
29. Kusarkar R, Goswami S, Tetrahedron 2004 60 5315
30. Rawat M, Wulff W D., Org. Lett. 2004 6 329
31. Yang C.-G, Wang J, Tang X.-X, Jiang B, Tetrahedron: Asymmetry 2002 13 383
32. For recent examples of syntheses of alkenyl-substituted heteroarenes by Suzuki-Miyaura-type reactions, see:, Singh B K., Cavalluzzo C, DeMaeyer M, Debyser Z, Parmar V S., VanderEycken E, Eur. J. Org. Chem. 2009 4589
33. Alacid E, Nájera C, J. Org. Chem. 2009 74 2321
34. Guillon J, Forfar I, Desplat V, Fabr S B., Thioplat D, Massip S, Carric H, Mossalayi D, Jarry C, J. Enz. Inhib. Med. Chem. 2007 22 541
35. Dragovich P S., Bertolini T M., Ayida B K., Li L.-S, Murphy D E., Rubsam F, Sun Z, Zhou Y, Tetrahedron 2007 63 1154
36. Molander G A., Brown A R., J. Org. Chem. 2006 71 9681
37. Molander G A., Fumagalli T, J. Org. Chem. 2006 71 5743
38. Capek P, Vrabel M, Hasnik Z, Pohl R, Hocek M, Synthesis 2006 3515
39. Azzam R, DeBorggraeve W M., Compernolle F, Hoornaert G J., Tetrahedron 2005 61 3953
40. Pyroux E, Berthiol F, Doucet H, Santelli M, Eur. J. Org. Chem. 2004 1075
41. Tan J, Chang J, Deng M, Synth. Commun. 2004 34 3773
42. Havelkova M, Dvorak D, Hocek M, Synthesis 2001 1704
43. For recent examples of syntheses of alkenyl-substituted heteroarenes by Stille-type couplings, see:, Masters K.-S, Flynn B L., Org. Biomol. Chem. 2010 8 1290
44. Enguehard-Guciffier C, Croix C, Hervet M, Kazock J.-Y, Gueiffier A, Abarbri M, Helv. Chim. Acta 2007 90 2349
45. Deska J, Kazmaier U, Angew. Chem. Int. Ed. 2007 46 4570
46. Gebauer J, Arseniyadis S, Cossy J, Org. Lett. 2007 9 3425
47. Dash J, Arseniyadis S, Cossy J, Adv. Synth. Catal. 2007 349 152
48. Roethle P A., Trauner D, Org. Lett. 2006 8 345
49. Wada A, Shinmen M, Uenishi J, Ito M, Lett. Org. Chem. 2006 3 817
50. Young G L., Smith S A., Taylor R J. K., Tetrahedron Lett. 2004 45 3797
51. Morice C, Garrido F, Mann A, Suffert J, Synlett 2002 501
52. Muratake H, Tonegawa M, Natsume M, Chem. Pharm. Bull. 1998 46 400
53. For examples of syntheses of alkenyl-substituted heteroarenes by Negishi-type couplings, see:, Luo F.-T, Hsieh L.-C, J. Org. Chem. 1996 61 9060
54. Bellina F, Carpita A, DeSantis M, Rossi R, Tetrahedron Lett. 1994 35 6913
55. Minato A, Suzuki K, Tamao K, Kumada M, Tetrahedron Lett. 1984 25 83
56. Negishi E, Luo F.-T, Frisbec R, Matsushita H, Heterocycles 1982 18 117
57. For leading references on the synthesis of alkenyl-substituted heteroarenes by Hiyama-type couplings, see
58. Chen J, Tanaka M, Sahoo A K., Takeda M, Yada A, Nakao Y, Hiyama T, Bull. Chem. Soc. Jpn. 2010 83 554
59. Alacid E, Nájera C, J. Org. Chem. 2008 73 2315
60. Nakao Y, Chen J, Tanaka M, Hiyama T, J. Am. Chem. Soc. 2007 129 11694
61. Itami K, Nokami T, Yoshida J.-i, J. Am. Chem. Soc. 2001 123 5600
62. Itami K, Mitsudo K, Kamei T, Koike T, Nokami T, Yoshida J.-i, J. Am. Chem. Soc. 2000 122 12013
63. For a book that introduces the reader to diverse aspects of the Mizoroki-Heck reaction, see: The Mizoroki-Heck Reaction Oestreich M John Wiley and Sons Hoboken 2009
64. For a synthesis of 6-acetylamino-3-ethenylpyridine realized on a multi-kilogram scale at Pfizer laboratories see:, Raggon J W., Snyder W M., Org. Process Res. Dev. 2002 6 811
65. Hussain M, Hung N T., Langer P, Tetrahedron Lett. 2009 50 3929
66. Cho C.-H, Neuenswander B, Lushington G H., Larock R C., J. Comb. Chem. 2008 10 941
67. Hughes C C., Trauner D, Tetrahedron 2004 60 9675
68. Hughes C C., Trauner D, Angew. Chem. Int. Ed. 2002 41 1569
69. Karminski-Zamola G, Dogan J, Bajic M, Blazevic J, Malesevic M, Heterocycles 1994 38 759
70. Crisp G T., Odonoghue A I., Synth. Commun. 1989 19 1745
71. Iranpoor N, Firouzabadi H, Tarassoli A, Fereidoonnezhad M, Tetrahedron 2010 66 2415
72. Toguem S M. T., Hussain M, Malik I, Villinger A, Langer P, Tetrahedron Lett. 2009 50 4962
73. Mitsudo K, Thansandote P, Wilhelm T, Mariampillai B, Lautens M, Org. Lett. 2006 8 3939
74. Berthiol F, Feurstein M, Doucet H, Santelli M, Tetrahedron Lett. 2002 43 5625
75. Pigeon P, Decoix B, Tetrahedron Lett. 1996 37 7707
76. Karabelas K, Hallberg A, J. Org. Chem. 1986 51 5286
77. Tamaru Y, Yamada Y, Yoshida Z.-i, Tetrahedron 1979 35 329
78. Hussain M, Malik I, Villinger A, Langer P, Synlett 2009 2691
79. Lage S, Martínez-Estíbalez U, Sotomayor N, Lete E, Adv. Synth. Catal. 2009 351 2460
80. Busacca C A., Dong Y, Tetrahedron Lett. 1996 37 3947
81. Hussain M, Tùng D T., Langer P, Synlett 2009 1822
82. Abbiati G, Beccalli E M., Broggini G, Zoni C, J. Org. Chem. 2003 68 7625
83. Beccalli E M., Broggini G, Marchesini A, Rossi E, Tetrahedron 2002 58 6673
84. Chacun-Lefevre L, Joseph B, Mérour J.-Y, Synlett 2001 848
85. Tokuyama H, Kaburagi Y, Chen X, Fukuyama T, Synthesis 2000 429
86. Malapel-Andrieu B, Mérour J.-Y, Tetrahedron 1998 54 11079
87. Yokoyama Y, Takahashi M, Takashima M, Kohno Y, Kobayashi H, Kataoka K, Shidori K, Murakami Y, Chem. Pharm. Bull. 1994 42 832
88. Gribble G W., Conway S C., Synth. Commun. 1992 22 2129
89. Merlic C M., Semmelhack M F., J. Organomet. Chem. 1990 391 C23
90. Harrington P J., Hegedus L S., McDaniel K F., J. Am. Chem. Soc. 1987 109 4335
91. Harrington P J., Hegedus L S., J. Org. Chem. 1984 49 2657
92. Deshpande R, Jiang L, Schmidt G, Rakovan J, Wang X, Wheeler K, Wang H, Org. Lett. 2009 11 4251
93. Yamashita M, Oda M, Hayashi K, Kawasaki I, Ohta S, Heterocycles 1998 48 2543
94. Benhida R, Lezama R, Fourrey J.-L, Tetrahedron Lett. 1998 39 5963
95. Díaz-Ortiz A, Prieto P, deCózar A, Cebrián C, Moreno A, delaHoz A, Aust. J. Chem. 2009 62 1600
96. Sakamoto T, Nagata H, Kondo Y, Shiraiwa M, Yamanaka H, Chem. Pharm. Bull. 1987 35 823
97. Deng J, Yong M, Chen Q.-Y, Synthesis 2005 2730
98. Collot V, Varlet D, Rault S, Tetrahedron Lett. 2000 41 4363
99. Ref. 12a., Loska R, Volla C, Vogel P, Adv. Synth. Catal. 2008 450 2859
100. Xu D, Liu Z, Tang W, Xu L, Hyder Z, Xiao J, Tetrahedron Lett. 2008 49 6104
101. Joubert N, Pohl R, Klepetárová B, Hocek M, J. Org. Chem. 2007 72 6797
102. Pei W, Mo J, Xiao J, J. Organomet. Chem. 2005 690 3546
103. Robert N, Hoarau C, Célanire S, Ribéreau P, Godard A, Quéguiner G, Marsais F, Tetrahedron 2005 61 4569
104. Keen S P., Cowden C J., Bishop B C., Brands K M. J., Davies A J., Dolling U H., Lieberman D R., Stuart G W., J. Org. Chem. 2005 70 1771
105. Karig G, Thasana N, Gallagher T, Synlett 2002 808
106. Banston D, Fang F, Huie E, Xie S, J. Org. Chem. 1999 64 3461
107. Anson M S., Mirza A R., Tonks L, Williams J M. J., Tetrahedron Lett. 1999 40 7147
108. Padwa A, Sheehan S M., Straub C S., J. Org. Chem. 1999 64 8648
109. Niu C, Li J, Doyle T W., Chen S.-H, Tetrahedron 1998 54 6311
110. Cho S Y., Kim S S., Park K.-H, Kang S K., Choi J.-K, Hwang K.-J, Yum E K., Heterocycles 1996 43 1641
111. Draper T L., Bailey T R., Synlett 1995 157
112. Bumagin N A., Bykov V V., Sukhomlinova L I., Tolstaya T P., Beletskaya I P., J. Organomet. Chem. 1995 486 259
113. Hirooka S, Tanbo Y, Takemura K, Nakahashi H, Matsuoka T, Kuroda S, Bull. Chem. Soc. Jpn. 1991 64 1431
114. Frank W C., Kim Y C., Heck R F., J. Org. Chem. 1978 43 2947
115. Vallin K S. A., Larhed M, Hallberg A, J. Org. Chem. 2001 66 4340
116. Omar W A. E., Hormi O E. O., Tetrahedron 2009 65 4422
117. Wang Z, Wang B, Wu J, J. Comb. Chem. 2007 9 811
118. Kwok T J., Virgilio J A., Org. Process Res. Dev. 2005 9 694
119. Glasnov T N., Stadlbauer W, Kappe C O., J. Org. Chem. 2005 70 3864
120. Legros J.-Y, Primault G, Fiaud J.-C, Tetrahedron 2001 57 2507
121. Wright S W., Hageman D L., McClure L D., J. Heterocycl. Chem. 1998 35 717
122. Moa M J. G., Besada P, Teran C, Synthesis 2006 3973
123. Wada A, Yamamoto Y, Hase T, Nagai S, Kanatomo S, Synthesis 1986 555
124. Akita Y, Ohta A, Heterocycles 1982 19 329
125. Sakamoto T, Arakida H, Edo K, Yamanake H, Heterocycles 1981 16 965
126. Edo K, Sakamoto T, Yamanaka H, Chem. Pharm. Bull. 1979 27 193
127. Coelho A, Sotelo E, Novoa H, Peeters O M., Blaton N, Raviña E, Tetrahedron Lett. 2004 45 3459
128. Wada A, Yasuda H, Kanatomo S, Synthesis 1988 771
129. Malik I, Hussain M, Ali A, Toguem S.-M T., Basha F Z., Fischer C, Langer P, Tetrahedron 2010 66 1637
130. Azzam P, DeBorggraevem W M., Compernolle F, Hoornaert G J., Tetrahedron 2005 61 3953
131. Akita Y, Noguchi T, Sugimoto M, Ohta A, J. Heterocycl. Chem. 1986 23 1481
132. Tobrman T, Dvorák D, Eur. J. Org. Chem. 2008 2923
133. Huang W S., Wang Y, Sundaramoorthi R, Thomas R M., Wen D, Liu S, Lentini S P., Das S, Banda G, Sawyer T K., Shakespeare W C., Tetrahedron Lett. 2007 48 7388
134. Jacobson K A., Shi D, Gallo-Rodriguez C, Manning M Jr., Müller C, Daly J W., Neumeyer J L., Kiriasis L, Pfleiderer W, J. Med. Chem. 1993 36 2639
135. Yin L, Liebscher J, Synthesis 2004 2329
136. Ferreira E M., Zhang H, Stoltz B M., Oxidative Heck-Type Reactions (Fujiwara-Moritani Reactions), In The Mizoroki-Heck Reaction Oestreich M John Wiley and Sons Hoboken 2009 Chap. 9 345-382
137. Karimi B, Behzadnia H, Elhamifar D, Akhavan P F., Esfahani F K., Zamani A, Synthesis 2010 1399
138. Myers A G., Tanaka D, Mannion M R., J. Am. Chem. Soc. 2002 124 11250
139. For a short review on the decarboxylative palladium-catalyzed cross-coupling reactions, see:, Baudoin O, Angew. Chem. Int. Ed. 2007 46 1373
140. Fujiwara Y, Kitamura T, Fujiwara Reaction: Palladium-Catalyzed Hydroarylation of Alkynes and Alkenes Dyker G Wiley-VCH Weinheim 2005
141. Pekel N, Güven O, Polym. Int. 2002 51 1404
142. Brustolin F, Castelvetro V, Ciardelli F, Ruggeri G, Colligiani A, J. Polym. Sci., Ser. A 2000 39 253
143. Trofimov B A., Mikhaleva A I., Morozowa L V., Russ. Chem. Rev. 1985 54 1034
144. Gipstein E, Hewett W A., Macromolecules 1969 2 82
145. Hormi O E. O., Hirvelä L, Tetrahedron Lett. 1993 34 6463
146. Gopal D, Rajagopalan K, Tetrahedron Lett. 1987 28 5237
147. Ogata M, Matsumoto H, Shimizu S, Kida S, Shiro M, Tawara K, J. Med. Chem. 1987 30 1348
148. Ross W J., Jamieson W B., McCowen M C., J. Med. Chem. 1973 16 347
149. Lebedev A Y., Izmuer V V., Kazylkin D N., Beletskaya I P., Voskoboynikov A Z., Org. Lett. 2002 4 623
150. Rainka M P., Aye Y, Buchwald S, Proc. Natl. Acad. Sci. U.S.A. 2004 101 5821
151. Wang Z, Bao W, Jiang Y, Chem. Commun. 2005 2849
152. Movassaghi M, Ondrus A E., J. Org. Chem. 2005 70 8638
153. Taillefer M, Ouali A, Renard B, Spindler J.-F, Chem. Eur. J. 2006 12 5301
154. Ouali A, Laurent R, Caminade A.-M, Majoral J.-P, Taillefer M, J. Am. Chem. Soc. 2006 128 15990
155. Shen G, Lv X, Qian W, Bao W, Tetrahedron Lett. 2008 49 4556
156. Reddy V P., Kumar A V., Rao K R., Tetrahedron Lett. 2010 in press
157. Bao W, Liu Y, Lv X, Synthesis 2008 1911
158. Liao Q, Wang Y, Zhang L, Xi C, J. Org. Chem. 2009 74 6371
159. Kaddouri H, Vicente V, Ouali A, Ouazzani F, Taillefer M, Angew. Chem. Int. Ed. 2009 48 333
160. Kabir M, Lorenz M, Namjoshi O A., Cook J M., Org. Lett. 2010 12 464
161. Burley G A., Davies D L., Griffith G A., Lee M, Singh K, J. Org. Chem. 2010 75 980
162. Mao J, Xie G, Zhan J, Hua Q, Shi D, Adv. Synth. Catal. 2009 351 1268
163. For reviews, see:, Roger J, Gottumukkala A L., Doucet H, ChemCatChem 2010 2 20
164. Ackermann L, Vicente R, Kapdi A R., Angew. Chem. Int. Ed. 2009 48 9792
165. Bellina F, Rossi R, Tetrahedron 2009 65 10269
166. Thansandote P, Lautens M, Chem. Eur. J. 2009 15 5874
167. Kulkarni A A., Daugulis O, Synthesis 2009 4087
168. Kakiuchi F, Kochi T, Synthesis 2008 3013
169. Campeau L.-C, Fagnou K, Chem. Soc. Rev. 2007 36 1058
170. Seregin I V., Gevorgyan V, Chem. Soc. Rev. 2007 107 1173
171. Alberico D, Scott M E., Lautens M, Chem. Rev. 2007 107 174
172. Satoh T, Miura M, Chem. Lett. 2007 36 200
173. Koubachi J, ElKazzouli S, Berteina-Raboin S, Mouaddib A, Guillaumet G, Synthesis 2008 2537
174. Gottumukkala A L., Derridj F, Djebbar S, Doucet H, Tetrahedron Lett. 2008 49 2926
175. Besselièvre F, Lebrequier S, Mahuteau-Betzer F, Piguel S, Synthesis 2009 3511
176. Besselièvre F, Piguel S, Mahuteau-Betzer F, Grierson D S., Org. Lett. 2008 10 4029
177. Verrier C, Hoarau C, Marsais F, Org. Biomol. Chem. 2009 7 647
178. Rodriguez A, Fennessy R, Moran W J., Tetrahedron Lett. 2009 50 3942
179. Spulák M, Luboiacky R, Senel P, Kunes J, Pour M, J. Org. Chem. 2010 75 241
180. Mousseau J J., Bull J A., Charette A B., Angew. Chem. Int. Ed. 2010 49 1115
181. Legault C, Charette A B., J. Org. Chem. 2003 68 7119
182. Ackermann L, Barfüsser S, Pospech J, Org. Lett. 2010 12 724
183. Patil A D., Freyer A J., Killmer L, Offen P, Carte B, Jurewicz A J., Johnson R K., Tetrahedron 1997 53 5047
184. Bellina F, Cauteruccio S, Rossi R, Eur. J. Org. Chem. 2006 1379
185. Bellina F, Calandri C, Cauteruccio S, Rossi R, Tetrahedron 2007 63 1970
186. Bellina F, Cauteruccio S, DiFiore A, Marchetti C, Rossi R, Tetrahedron 2008 64 6060
187. Cerna I, Pohl R, Klepetárová B, Hocek M, Org. Lett. 2006 8 5839
188. Sahnoun S, Messaoudi S, Peyrat J.-F, Brion J D., Alami M, Tetrahedron Lett. 2008 49 7279
189. Axelrod V, Belzile J R., J. Org. Chem. 1958 23 919
190. Arcadi A, Alfonsi M, Marinelli F, J. Organomet. Chem. 2007 692 5322
191. Asano R, Moritani I, Fujiwara Y, Teranishi S, Bull. Chem. Soc. Jpn. 1973 46 663
192. Maruyama O, Fujiwara Y, Taniguchi H, Bull. Chem. Soc. Jpn. 1981 54 2851
193. Fujiwara Y, Maruyama O, Yoshidomi M, Taniguchi H, J. Org. Chem. 1981 46 851
194. Itahara T, Ikeda M, Sakakibara T, J. Chem. Soc., Perkin Trans. 1 1983 1361
195. Hirota K, Isobe Y, Kitade Y, Maki Y, Synthesis 1987 495
196. Yokoyama Y, Matsumoto T, Murakami Y, J. Org. Chem. 1995 60 1486
197. Jia C, Kitamura T, Fujiwara Y, Acc. Chem. Res. 2001 34 633
198. Moritani I, Fujiwara Y, Synthesis 1973 524
199. Maruyama O, Yoshidomi M, Fujiwara Y, Taniguchi H, Chem. Lett. 1979 1229
200. Tsuji J, Nagashima H, Tetrahedron 1984 40 2699
201. Itahara T, Kawasaki K, Ouseto F, Bull. Chem. Soc. Jpn. 1984 57 3488
202. Itahara T, Kawasaki K, Ouseto F, Synthesis 1984 236
203. Jia C, Lu W, Kitamura T, Fujiwara Y, Org. Lett. 1999 1 2097
204. Yokoyama Y, Tsuruta K, Murakami Y, Heterocycles 2002 56 525
205. Yokota T, Tani M, Sakaguchi S, Ishii Y, J. Am. Chem. Soc. 2003 125 1476
206. Capito E, Brown J M., Ricci A, Chem. Commun. 2005 1854
207. Fanton G, Coles N M., Cowley A R., Fleming J P., Brown J M., Heterocycles 2010 80 895
208. Grimster N P., Gauntlett C, Godfrey C R. A., Gaunt M J., Angew. Chem. Int. Ed. 2005 44 3125
209. Beck E M., Grimster N P., Hatley R, Gaunt M J., J. Am. Chem. Soc. 2006 128 2528
210. Trofimov B A., Sobenina L N., Mikhaleva A I., Chem. Rev. 2004 104 2481
211. Djakovitch L, Rouge P, J. Mol. Catal. A: Chem. 2007 273 230
212. Maehara A, Tsurugi H, Satoh T, Miura M, Org. Lett. 2008 10 1159
213. Cho S H., Hwang S J., Chang S, J. Am. Chem. Soc. 2008 130 9254
214. Beck E M., Hatley R, Gaunt M J., Angew. Chem. Int. Ed. 2008 47 3004
215. Maehara A, Satoh T, Miura M, Tetrahedron 2008 64 5987
216. Cheng D, Gallagher T, Org. Lett. 2009 11 2639
217. Zhao J, Huang L, Cheng K, Zhang Y, Tetrahedron Lett. 2009 50 2758
218. Koubachi J, Berteina-Raboin S, Mouaddib A, Guillaumet G, Synthesis 2009 271
219. Djakovitch L, Rouge P, Catal. Today 2009 140 90
220. Wu J, Cui X, Chen L, Jiang G, Wu Y, J. Am. Chem. Soc. 2009 131 13888
221. Yang Y, Zhang Y, Org. Lett. 2009 11 5606
222. Jiang H, Feng Z, Wang A, Liu X, Chen Z, Eur. J. Org. Chem. 2010 1227
223. García-Rubia A, Arrayás R G., Carretero J C., Angew. Chem. Int. Ed. 2009 48 6511
224. Nakao Y, Nashihara N, Kanyiva K S., Hiyama T, J. Am. Chem. Soc. 2008 130 16170
225. Zhang Y.-H, Shi B.-F, Yu J.-Q, J. Am. Chem. Soc. 2009 131 5072
226. Jia C, Piao D, Oyamada J, Lu W, Kitamura T, Fujiwara Y, Science 2000 287 1992
227. Mitchell D, Yu H, Curr. Opin. Drug Discovery 2003 6 876
228. Nevado C, Echavarren A M., Synthesis 2005 167
229. Fujiwara Y, Kitamura T, Fujiwara Reaction: Palladium-Catalyzed Hydroarylation of Alkynes and Alkenes, In Handbook of C-H Transformations. Applications in Organic Synthesis Vol. II Dyker G Wiley-VCH Weinheim 2005 194-202
230. Kitamura T, Eur. J. Org. Chem. 2009 1111
231. Vasilev A V., Russ. J. Org. Chem. 2009 45 1
232. Wang X, Zhou L, Lu W, Curr. Org. Chem. 2010 14 289
233. Koninobu Y, Kikuchi K, Tokunaga Y, Nishina Y, Takai K, Tetrahedron 2008 64 5974
234. Yi C S., Zhang J, Chem. Commun. 2008 2349
235. Guo R, Yi C S., J. Org. Chem. 2010 75 3144
236. Hong P, Cho B.-R, Yamazaka H, Chem. Lett. 1980 507
237. Mukai T, Hirano K, Satoh T, Miura M, J. Org. Chem. 2009 74 6410
238. Kanyiva K S., Nakao Y, Hiyama T, Heterocycles 2007 72 677
239. Nakao Y, Kanyiva K S., Oda S, Hiyama T, J. Am. Chem. Soc. 2006 128 8146
240. Kanyiva K S., Nakao Y, Hiyama T, Angew. Chem. Int. Ed. 2007 46 8872
241. Nakao Y, Kanyiva K S., Hiyama T, J. Am. Chem. Soc. 2008 130 2448
242. Nakao Y, Idei H, Kanyiva K S., Hiyama T, J. Am. Chem. Soc. 2009 131 15996
243. Kanyiva K S., Löbermann F, Nakao Y, Hiyama T, Tetrahedron Lett. 2009 50 3463
244. Lu W, Jia C, Kitamura T, Fujiwara Y, Org. Lett. 2000 2 2927
245. Oyamada J, Lu W, Jia C, Kitamura T, Fujiwara Y, Chem. Lett. 2002 20
246. Tsukada N, Murata K, Inoue Y, Tetrahedron Lett. 2005 46 7515
247. Oyamada J, Kitamura T, Tetrahedron 2009 65 3482
248. Reetz M T., Sommer K, Eur. J. Org. Chem. 2003 3485
249. For a review, see:, Nakao Y, Hiyama T, Pure Appl. Chem. 2008 80 1097
250. Nakao Y, Oda S, Hiyama T, J. Am. Chem. Soc. 2004 126 13904
251. Nakao Y, Oda S, Yada A, Hiyama T, Tetrahedron 2006 62 7567
252. Nakao Y, Yoda A, Ebata A, Hiyama T, J. Am. Chem. Soc. 2007 129 2428
253. For recent examples of syntheses of fine chemicals and their precursors by scalable Mizoroki-Heck reactions see
254. Gøgsig T M., Lindhardt A T., Dekhane M, Grouleff J, Skrydstrup T, Chem. Eur. J. 2009 15 5950
255. Zegar S, Tokar C, Enache L A., Rajagopoi V, Zeller W, OConnell M, Singh J, Muellner F W., Zembower D E., Org. Process Res. Dev. 2007 11 747
256. Prashad M, Top. Organomet. Chem. 2004 6 181
257. For leading references on the synthesis of E -alkenyl halides, see:, Ren K, Wang M, Wang L, Eur. J. Org. Chem. 2010 565
258. Yao M.-L, Quick T R., Wu Z, Quinn M P., Kabalka G W., Org. Lett. 2009 11 2647
259. Das B, Venkataswarlu K, Krishnaiah M, Holla H, Maji A, Helv. Chim. Acta 2006 89 1417
260. Hoshi M, Tanaka H, Shirakawa K, Arase A, Chem. Commun. 1999 627
261. Zou M.-F, Deng M.-Z, J. Org. Chem. 1996 61 1857
262. Kamiya N, Yoshihiro Y, Ishii Y, Synlett 1990 675
263. Brown H C., Hamaoka T, Ravindran N, Subrahmanyan C, Somayaji V, Bhat N, J. Org. Chem. 1989 54 6075
264. For leading references on the synthesis of Z -alkenyl halides, see
265. Lebrun M.-E, LeMarquand P, Berthelette C, J. Org. Chem. 2006 71 2009
266. Kuang C, Yang Q, Senboku H, Tokuda M, Tetrahedron 2005 61 4043
267. Kadota I, Ueno H, Ohno A, Yamamoto Y, Tetrahedron Lett. 2003 44 8645
268. Baati R, Barma D K., Krishna U M., Mioskowski C, Falck J R., Tetrahedron Lett. 2002 43 959
269. Kuang C, Senboku H, Tokuda M, Tetrahedron Lett. 2001 42 3893
270. Uenishi J, Kawahama R, Yanemitsu O, Tsuji J, J. Org. Chem. 1998 63 8965
271. Uenishi J, Kawahama R, Shiga Y, Yonemitsu O, Tsuji J, Tetrahedron Lett. 1996 37 6759
272. Stork G, Zhao K, Tetrahedron Lett. 1989 30 2173
273. Brown H C., Somayaji V, Synthesis 1984 919