Rhodium-catalyzed [2+2+2] cycloaddition of alkynes for the synthesis of substituted benzenes: Catalysts, reaction scope, and synthetic applications

Synthesis

Volumn 44, Issue 3, 2012, Pages 323-350

  Shibata, Yu ^a   Tanaka, Ken ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

alkynes; benzenes; catalysis; cycloaddition; rhodium

Indexed keywords

[2+2+2] CYCLOADDITION; ALKYNES; BIARYLS; BIOLOGICALLY ACTIVE COMPOUNDS; CYCLOADDITION REACTION; CYCLOPHANES; INTERMOLECULAR REACTIONS; INTRAMOLECULAR REACTIONS; ORGANIC MATERIALS; ORGANOPHOSPHORUS COMPOUNDS; RHODIUM COMPLEXES; RHODIUM-CATALYZED; SUBSTITUTED BENZENES; SYNTHETIC APPLICATION;

ACETYLENE; BENZENE; BENZENE REFINING; BIOACTIVITY; CATALYSIS; CONDENSATION REACTIONS; CYCLOADDITION; ORGANIC POLYMERS; PHOSPHORUS COMPOUNDS; RHODIUM; RHODIUM COMPOUNDS; TRANSITION METALS;

SYNTHESIS (CHEMICAL);

ALKYNE DERIVATIVE; BENZENE DERIVATIVE; BIARYL DERIVATIVE; CYCLOPHANE DERIVATIVE; FULLERENE; HELICENE; ORGANIC COMPOUND; ORGANOPHOSPHORUS COMPOUND; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLOADDITION; ENANTIOSELECTIVITY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84856230859     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289665     Document Type: Article

References (196)

1. For recent reviews and accounts, see:, Weding N, Hapke M, Chem. Soc. Rev. 2011 40 4525
2. Hua R, Abrenica M V. A., Wang P, Curr. Org. Chem. 2011 15 712
3. Gulias M, Lopez F, Mascarenas J L., Pure Appl. Chem. 2011 83 495
4. Shaaban M R., El-Sayed R, Elwahy A H. M., Tetrahedron 2011 67 6095
5. Li S, Zhou L, Kanno K.-i, Takahashi T, J. Heterocycl. Chem. 2011 48 517
6. Dominguez G, Perez-Castells J, Chem. Soc. Rev. 2011 40 3430
7. Zhou L, Li S, Kanno K.-i, Takahashi T, Heterocycles 2010 80 725
8. Inglesby P A., Evans P A., Chem. Soc. Rev. 2010 39 2791
9. Tanaka K, Chem. Asian J. 2009 4 508
10. Perreault S, Rovis T, Chem. Soc. Rev. 2009 38 3149
11. Galan B R., Rovis T, Angew. Chem. Int. Ed. 2009 48 2830
12. Zhou L, Yamanaka M, Kanno K.-i, Takahashi T, Heterocycles 2008 76 923
13. Varela J A., Sa C, Synlett 2008 2571
14. Shibata T, Tsuchikama K, Org. Biomol. Chem. 2008 6 1317
15. Yamamoto Y, Chim. Oggi 2007 25 108
16. Tanaka K, Synlett 2007 1977
17. Heller B, Hapke M, Chem. Soc. Rev. 2007 36 1085
18. Agenet N, Buisine O, Slowinski F, Gandon V, Aubert C, Malacria M, Org. React. (N. Y.) 2007 68 1
19. Chopade P R., Louie J, Adv. Synth. Catal. 2006 348 2307
20. Yamamoto Y, Curr. Org. Chem. 2005 9 503
21. Kotha S, Brahmachary E, Lahiri K, Eur. J. Org. Chem. 2005 4741
22. Gandon V, Aubert C, Malacria M, Curr. Org. Chem. 2005 9 1699
23. Fujiwara M, Ojima I, Rhodium(I)-catalyzed cycloisomerization and cyclotrimerization reactions, In Modern Rhodium-Catalyzed Organic Reactions Evans P A. Wiley-VCH Weinheim 2005 Chap. 7 129
24. Varela J A., Sa C, Chem. Rev. 2003 103 3787
25. Reppe W, Sweckendiek W J., Justus Liebigs Ann. Chem. 1948 560 104
26. For a review of the transition-metal-catalyzed enantio-selective synthesis of compounds with non-centrochirality, see:, Ogasawara M, Watanabe S, Synthesis 2009 1761
27. For a review of the transition-metal-catalyzed enantio-selective [2+2+2]-cycloaddition reactions for the synthesis of axially chiral biaryls, see ref. 1i.
28. Mller E, Synthesis 1974 761
29. Grigg R, Scott R, Stevenson P, Tetrahedron Lett. 1982 23 2691
30. Grigg R, Scott R, Stevenson P, J. Chem. Soc., Perkin Trans. 1 1988 1357
31. Tanaka K, Shirasaka K, Org. Lett. 2003 5 4697
32. For reports involving mechanistic studies, see:, Orian L, VanStralen J N. P., Bickelhaupt F M., Organometallics 2007 26 3816
33. Dachs A, Torrent A, Pla-Quintana A, Roglans A, Jutand A, Organometallics 2009 28 6036
34. Dachs A, Torrent A, Roglans A, Parella T, Osuna S, Sola M, Chem. Eur. J. 2009 15 5289
35. Collman J P., Kang J W., Little W F., Sullivan M F., Inorg. Chem. 1968 7 1298
36. Cash G G., Helling J F., Mathew M, Palenik G J., J. Organomet. Chem. 1973 50 277
37. Caddy P, Green M, OBrien E, Smart L E., Woodward P, J. Chem. Soc., Dalton Trans. 1980 962
38. Abdulla K, Booth B L., Stacey C, J. Organomet. Chem. 1985 293 103
39. Booth B L., Ofunne G C., Stacey C, Tait P J. T., J. Organomet. Chem. 1986 315 143
40. Yan H, Beatty A M., Fehlner T P., Organometallics 2002 21 5029
41. Toganoh M, Matsuo Y, Nakamura E, J. Organomet. Chem. 2003 683 295
42. Krampe O, Song C E., Klui W, Organometallics 1993 12 4949
43. Garcia J J., Sierra C, Torrens H, Tetrahedron Lett. 1996 37 6097
44. Field L D., Ward A J., Turner P, Aust. J. Chem. 1999 52 1085
45. Uozumi Y, Nakazono M, Adv. Synth. Catal. 2002 344 274
46. Amer I, Bernstein T, Eisen M, Blum J, Vollhardt K P. C., J. Mol. Catal. 1990 60 313
47. Yoshida K, Morimoto I, Mitsudo K, Tanaka H, Chem. Lett. 2007 36 998
48. Yoshida K, Morimoto I, Mitsudo K, Tanaka H, Tetrahedron 2008 64 5800
49. Yoshida K, Morimoto I, Mitsudo K, Tanaka H, Tetrahedron Lett. 2008 49 2363
50. Amer I, Blum J, Vollhardt K P. C., J. Mol. Catal. 1990 60 323
51. Taber D F., Rahimizadeh M, Tetrahedron Lett. 1994 35 9139
52. Konno T, Moriyasu K, Kinugawa R, Ishihara T, Org. Biomol. Chem. 2010 8 1718
53. Yoshikawa S, Kiji J, Furukawa J, Makromol. Chem. 1977 178 1077
54. Carlton L, Read G, J. Chem. Soc., Perkin Trans. 1 1978 1631
55. Aresta M, DeFazio M, J. Organomet. Chem. 1980 186 109
56. Albano P, Aresta M, J. Organomet. Chem. 1980 190 243
57. Shestakova V S., Shestakov G K., Yureva L P., Belyi A A., Temkin O N., Izv. Akad. Nauk SSSR, Ser. Khim. 1985 534
58. Pillai S M., Ohnishi R, Ichikawa M, J. Chem. Soc., Chem. Commun. 1990 246
59. Wendt J, Klinger U, Singer H, Inorg. Chim. Acta 1991 183 133
60. Baidossi W, Goren N, Blum J, Schumann H, Holger H, J. Mol. Catal. 1993 85 153
61. Doyle M P., Shanklin M S., Organometallics 1994 13 1081
62. Setty-Fichman M, Blum J, Sasson Y, Eisen M, Tetrahedron Lett. 1994 35 781
63. Badrieh Y, Greenwald A, Schumann H, Blum J, Chem. Ber. 1992 125 667
64. McDonald F E., Zhu H Y. H., Holmquist C R., J. Am. Chem. Soc. 1995 117 6605
65. Kotha S, Brahmachary E, Tetrahedron Lett. 1997 38 3561
66. Kotha S, Sreenivasachary N, Bioorg. Med. Chem. Lett. 2000 10 1413
67. Witulski B, Stengel T, Angew. Chem. Int. Ed. 1999 38 2426
68. Witulski B, Alayrac C, Angew. Chem. Int. Ed. 2002 41 3281
69. Witulski B, Stengel T, Angew. Chem. Int. Ed. 1998 37 489
70. Witulski B, Zimmermann A, Synlett 2002 1855
71. Dufkov L, Csaov I,, tepnika P, Kotora M, Eur. J. Org. Chem. 2003 2882
72. Novk P, Pohl R, Kotora M, Hocek M, Org. Lett. 2006 8 2051
73. Novk P, halov S, Otmar M, Hocek M, Kotora M, Tetrahedron 2008 64 5200
74. Torrent A, Gonzlez I, Pla-Quintana A, Roglans A, Moreno-Manas M, Parella T, Benet-Buchholz J, J. Org. Chem. 2005 70 2033
75. Gonzlez I, Bouquillon S, Roglans A, Muzart J, Tetrahedron Lett. 2007 48 6425
76. Brun S, Garcia L, Gonzlez I, Torrent A, Dachs A, Pla-Quintana A, Parella T, Roglans A, Chem. Commun. 2008 4339
77. Wu Y.-T, Linden A, Siegel J S., Org. Lett. 2005 7 4353
78. Wu Y.-T, Hayama T, Baldridge K K., Linden A, Siegel J S., J. Am. Chem. Soc. 2006 128 6870
79. Arimitsu S, Hammond G B., J. Org. Chem. 2006 71 8665
80. Garcia L, Pla-Quintana A, Roglans A, Org. Biomol. Chem. 2009 7 5020
81. Sun Q, Zhou X, Islam K, Kyle D J., Tetrahedron Lett. 2001 42 6495
82. Young D D., Senaiar R S., Deiters A, Chem. Eur. J. 2006 12 5563
83. Grigg R, Sridharan V, Zhang J, Tetrahedron Lett. 1999 40 8277
84. Grigg R, Savic V, Tambyrajah V, Tetrahedron Lett. 2000 41 3003
85. Grigg R, Sridharan V, Wang J, Xu J, Tetrahedron 2000 56 8967
86. Bonfield E R., Li C.-J, Adv. Synth. Catal. 2008 350 370
87. Nishiyama H, Niwa E, Inoue T, Ishima Y, Aoki K, Organometallics 2002 21 2572
88. Uchimura H, Ito J.-i, Iwasa S, Nishiyama H, J. Organomet. Chem. 2007 692 481
89. Kinoshita H, Shinokubo H, Oshima K, J. Am. Chem. Soc. 2003 125 7784
90. Gonzalez I, Pla-Quintana A, Roglans A, Synlett 2009 2844
91. Wang Y.-H, Huang S.-H, Lin T.-C, Tsai F.-Y, Tetrahedron 2010 66 7136
92. Wu W, Zhang X Y., Kang S X., Chin. Chem. Lett. 2010 21 18
93. Grigg R, Kilner C, Senthilnanthanan M, Seabourne C R., Sridharan V, Murrer B A., ARKIVOC 2007 (xi) 145
94. Ojima I, Vu A T., McCullagh J V., Kinoshita A, J. Am. Chem. Soc. 1999 121 3230
95. Chin C S., Won G, Song J, Bull. Korean Chem. Soc. 1994 15 961
96. Tani K, Ueda K, Arimitsu K, Yamagata T, Kataoka Y, J. Organomet. Chem. 1998 560 253
97. Tanaka K, Toyoda K, Wada A, Shirasaka K, Hirano M, Chem. Eur. J. 2005 11 1145
98. Tanaka K, Nishida G, Ogino M, Hirano M, Noguchi K, Org. Lett. 2005 7 3119
99. Tanaka K, Hara H, Nishida G, Hirano M, Org. Lett. 2007 9 1907
100. Komine Y, Miyauchi Y, Kobayashi M, Tanaka K, Synlett 2010 3092
101. Hara H, Hirano M, Tanaka K, Org. Lett. 2008 10 2537
102. Hara H, Hirano M, Tanaka K, Tetrahedron 2009 65 5093
103. Tanaka K, Osaka T, Noguchi K, Hirano M, Org. Lett. 2007 9 1307
104. Hara H, Hirano M, Tanaka K, Org. Lett. 2009 11 1337
105. Zhang K, Louie J, J. Org. Chem. 2011 76 4686
106. Komine Y, Kamisawa A, Tanaka K, Org. Lett. 2009 11 2361
107. Tanaka K, Sawada Y, Aida Y, Thammathevo M, Tanaka R, Sagae H, Otake Y, Tetrahedron 2010 66 1563
108. Jung M E., Piizzi G, Chem. Rev. 2005 105 1735
109. Noguchi H, Hojo K, Suginome M, J. Am. Chem. Soc. 2007 129 758
110. Iannazzo L, Vollhardt K P. C., Malacria M, Aubert C, Gandon V, Eur. J. Org. Chem. 2011 2011 3283
111. Brun S, Parera M, Pla-Quintana A, Roglans A, Len T, Achard T, Sol J, Verdaguer X, Riera A, Tetrahedron 2010 66 9032
112. For reviews of cyclophanes, see: Cyclophane Chemistry Vögtle F Wiley Chichester 1993
113. Modern Cyclophane Chemistry Gleiter R Hopf H Wiley-VCH Weinheim 2004
114. For reviews of cyclophane synthesis, see
115. Kane V V., DeWolf W H., Bickelhaupt F, Tetrahedron 1994 50 4574
116. See also ref. 3.
117. Tanaka K, Sagae H, Toyoda K, Noguchi K, Eur. J. Org. Chem. 2006 3575
118. Tanaka K, Sagae H, Toyoda K, Noguchi K, Hirano M, J. Am. Chem. Soc. 2007 129 1522
119. Tanaka K, Sagae H, Toyoda K, Hirano M, Tetrahedron 2008 64 831
120. Shibata T, Uchiyama T, Endo K, Org. Lett. 2009 11 3906
121. Araki T, Hojo D, Noguchi K, Tanaka K, Synlett 2011 539
122. For representative reviews of axially chiral biaryl ligands and catalysts, see:, Noyori R, Takaya H, Acc. Chem. Res. 1990 23 345
123. Shimizu H, Nagasaki I, Saito T, Tetrahedron 2005 61 5405
124. Hayashi T, Acc. Chem. Res. 2000 33 354
125. Minnaard A J., Feringa B L., Lefort L, deVries J G., Acc. Chem. Res. 2007 40 1267
126. Brunel J M., Chem. Rev. 2005 105 857
127. Hashimoto T, Maruoka K, Chem. Rev. 2007 107 5656
128. Akiyama T, Chem. Rev. 2007 107 5744
129. Terada M, Synthesis 2010 1929
130. For recent reviews of atropselective biaryl synthesis, see
131. Bringmann G, Mortimer A J. P., Keller P A., Gresser M J., Garner J, Breuning M, Angew. Chem. Int. Ed. 2005 44 5384
132. Baudoin O, Eur. J. Org. Chem. 2005 4223
133. Wallace T W., Org. Biomol. Chem. 2006 4 3197
134. Kozlowski M C., Morgan B J., Linton E C., Chem. Soc. Rev. 2009 38 3193
135. See also ref. 3.
136. Gutnov A, Heller B, Fischer C, Drexler H.-J, Spannenberg A, Sundermann B, Sundermann C, Angew. Chem. Int. Ed. 2004 43 3795
137. Shibata T, Fujimoto T, Yokota K, Takagi K, J. Am. Chem. Soc. 2004 126 8382
138. Tanaka K, Nishida G, Wada A, Noguchi K, Angew. Chem. Int. Ed. 2004 43 6510
139. Ogaki S, Shibata Y, Noguchi K, Tanaka K, J. Org. Chem. 2011 76 1926
140. Sakiyama N, Hojo D, Noguchi K, Tanaka K, Chem. Eur. J. 2011 17 1428
141. Tanaka K, Suda T, Noguchi K, Hirano M, J. Org. Chem. 2007 72 2243
142. Tanaka K, Kamisawa A, Suda T, Noguchi K, Hirano M, J. Am. Chem. Soc. 2007 129 12078
143. Nishida G, Suzuki N, Noguchi K, Tanaka K, Org. Lett. 2006 8 3489
144. Nishida G, Ogaki S, Yusa Y, Yokozawa T, Noguchi K, Tanaka K, Org. Lett. 2008 10 2849
145. Shibata T, Chiba T, Hirashima H, Ueno Y, Endo K, Heteroat. Chem. 2011 22 363
146. Imamoto T, Sugita K, Yoshida K, J. Am. Chem. Soc. 2005 127 11934
147. Shibata T, Chiba T, Hirashima H, Ueno Y, Endo K, Angew. Chem. Int. Ed. 2009 48 8066
148. Tanaka K, Takeishi K, Noguchi K, J. Am. Chem. Soc. 2006 128 4586
149. Tanaka K, Takahashi Y, Suda T, Hirano M, Synlett 2008 1724
150. Tracey M R., Oppenheimer J, Hsung R P., J. Org. Chem. 2006 71 8629
151. Oppenheimer J, Hsung R P., Figueroa R, Johnson W L., Org. Lett. 2007 9 3969
152. Oppenheimer J, Johnson W L., Figueroa R, Hayashi R, Hsung R P., Tetrahedron 2009 65 5001
153. Suda T, Noguchi K, Hirano M, Tanaka K, Chem. Eur. J. 2008 14 6593
154. Nishida G, Noguchi K, Hirano M, Tanaka K, Angew. Chem. Int. Ed. 2007 46 3951
155. Kondoh A, Yorimitsu H, Oshima K, J. Am. Chem. Soc. 2007 129 6996
156. Kobatake T, Kondoh A, Yoshida S, Yorimitsu H, Oshima K, Chem. Asian J. 2008 3 1613
157. Doherty S, Knight J G., Smyth C H., Harrington R W., Clegg W, Org. Lett. 2007 9 4925
158. Doherty S, Smyth C H., Harrington R W., Clegg W, Organometallics 2008 27 4837
159. Mori F, Fukawa N, Noguchi K.-I, Tanaka K, Org. Lett. 2011 13 362
160. Imamoto T, Saitoh Y, Koide A, Ogura T, Yoshida K, Angew. Chem. Int. Ed. 2007 46 8636
161. Nishida G, Noguchi K, Hirano M, Tanaka K, Angew. Chem. Int. Ed. 2008 47 3410
162. Rajca A, Miyasaka M, In Functional Organic Materials: Syntheses, Strategies, and Applications Mller T J. J. Bunz U H. F. Wiley-VCH Weinheim 2007 543
163. For recent reviews of helicene synthesis, see
164. Urbano A, Angew. Chem. Int. Ed. 2003 42 3986
165. See also ref. 3.
166. Tanaka K, Fukawa N, Suda T, Noguchi K, Angew. Chem. Int. Ed. 2009 48 5470
167. Fukawa N, Osaka T, Noguchi K, Tanaka K, Org. Lett. 2010 12 1324
168. Severa L, Adriaenssens L, Vvra J, Saman D, Csaov I, Fiedler P, Tepl F, Tetrahedron 2010 66 3537
169. Neeson S J., Stevenson P J., Tetrahedron Lett. 1988 29 813
170. Neeson S J., Stevenson P J., Tetrahedron 1989 45 6239
171. For a review, see:, Rohr J, Thiericke R, Nat. Prod. Rep. 1992 9 103
172. Kotha S, Mohanraja K, Durani S, Chem. Commun. 2000 1909
173. Witulski B, Zimmermann A, Gowans N D., Chem. Commun. 2002 2984
174. Welsch T, Tran H.-A, Witulski B, Org. Lett. 2010 12 5644
175. Anderson E A., Alexanian E J., Sorensen E J., Angew. Chem. Int. Ed. 2004 43 1998
176. Ramana C V., Salian S R., Gonnade R G., Eur. J. Org. Chem. 2007 5483
177. For reviews, see:, Markaryan E A., Samodurova A G., Russ. Chem. Rev. 1989 58 479
178. Larghi E L., Kaufman T S., Synthesis 2006 187
179. Ramana C V., Suryawanshi S B., Tetrahedron Lett. 2008 49 445
180. Alayrac C, Schollmeyer D, Witulski B, Chem. Commun. 2009 1464
181. For a review, see:, Jordan M A., Wilson L, Nat. Rev. Cancer 2004 4 253
182. Nicolaus N, Strauss S, Neudörfl J.-M, Prokop A, Schmalz H.-G, Org. Lett. 2009 11 341
183. Bugaut X, Guinchard X, Roulland E, J. Org. Chem. 2010 75 8190
184. Sedlk D, Novk P, Kotora M, Bartnk P, J. Med. Chem. 2010 53 4290
185. For reviews, see:, Berresheim A J., Mueller M, Muellen K, Chem. Rev. 1999 99 1747
186. Gin D L., Conticello V P., Trends Polym. Sci. 1996 4 217
187. Kovacic P, Jones M B., Chem. Rev. 1987 87 357
188. McDonald F E., Smolentsev V, Org. Lett. 2002 4 745
189. For a review, see:, Guldi D M., Chem. Soc. Rev. 2002 31 22
190. For a review, see:, Bendikov M, Wudl F, Perepichka D F., Chem. Rev. 2004 104 4891
191. Taillemite S, Fichou D, Eur. J. Org. Chem. 2004 4981
192. Traber B, Wolff J J., Rominger F, Oeser T, Gleiter R, Goebel M, Wortmann R, Chem. Eur. J. 2004 10 1227
193. Taylor M S., Swager T M., Org. Lett. 2007 9 3695
194. Kaseyama T, Furumi S, Zhang X, Tanaka K, Takeuchi M, Angew. Chem. Int. Ed. 2011 50 3684
195. Wu T.-C, Hsin H.-J, Kuo M.-Y, Li C.-H, Wu Y.-T, hJ. Am. Chem. Soc. 2011 133 16319
196. For our account of the cationic rhodium(I)-biaryl bisphosphine complex catalyzed [2+2+2]-cycloaddition reactions, see ref. 1p.