Metal-catalyzed carbonylation of alkynes: Key aspects and recent development

Tetrahedron Letters

Volumn 56, Issue 21, 2015, Pages 2634-2650

  Quintero Duque, Samuel ^a   Dyballa, Katrin Marie ^b   Fleischer, Ivana ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b EVONIK INDUSTRIES AG   (Germany)

Author keywords

Homogeneous catalysis Carbonylation Alkynes Hydroesterification Pauson Khand reaction

Indexed keywords

EID: 84937762579     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.04.043     Document Type: Review

References (198)

1. L. Kollár Modern Carbonylation Methods 2008 Wiley-VCH Verlag Weinheim
2. M. Beller Catalytic Carbonylation Reactions 2006 Springer Verlag Berlin Heidelberg
3. G. Kiss Chem. Rev. 101 2001 3435
4. W. Reppe Justus Liebigs Ann. Chem. 582 1953 116
5. W. Reppe Justus Liebigs Ann. Chem. 582 1953 1
6. W. Reppe, and H. Vetter Justus Liebigs Ann. Chem. 582 1953 133
7. Reppe, W. DE855110, 1939.
8. X.-F. Wu, H. Neumann, and M. Beller Chem. Rev. 113 2012 1
9. B. Gabriele, G. Salerno, and M. Costa Synlett 2004 2468
10. A. Brennführer, H. Neumann, and M. Beller ChemCatChem 1 2009 28
11. R. Chinchilla, and C. Najera Chem. Rev. 114 2014 1783
12. X.-F. Wu, H. Neumann, and M. Beller ChemSusChem 6 2013 229
13. W. Fang, H. Zhu, Q. Deng, S. Liu, X. Liu, Y. Shen, and T. Tu Synthesis 46 2014 1689
14. T. Nogi, and J. Tsuji Tetrahedron 25 1969 4099
15. J. Tsuji, and T. Nogi Tetrahedron Lett. 1966 1801 7
16. B. El Ali, and H. Alper J. Mol. Catal. 67 1991 29
17. K. Itoh, M. Miura, and M. Nomura Tetrahedron Lett. 33 1992 5369
18. D. Zargarian, and H. Alper Organometallics 12 1993 712
19. B.E. Ali, and H. Alper J. Mol. Catal. A: Chem. 96 1995 197
20. M. Akao, S. Sugawara, K. Amino, and Y. Inoue J. Mol. Catal. A: Chem. 157 2000 117
21. E. Drent, P. Arnoldy, and P.H.M. Budzelaar J. Organomet. Chem. 455 1993 247
22. F. Cavani, and J.H. Teles ChemSusChem 2 2009 508
23. J.F. Knifton J. Mol. Catal. 2 1977 293
24. B. El Ali, J. Tijani, and A.M. El-Ghanam Tetrahedron Lett. 42 2001 2385
25. A.A. Nunez Magro, L.-M. Robb, P.J. Pogorzelec, A.M.Z. Slawin, G.R. Eastham, and D.J. Cole-Hamilton Chem. Sci. 1 2010 723
26. A. Scrivanti, V. Beghetto, E. Campagna, M. Zanato, and U. Matteoli Organometallics 17 1998 630
27. A. Dervisi, P.G. Edwards, P.D. Newman, R.P. Tooze, S.J. Coles, and M.B. Hursthouse J. Chem. Soc., Dalton Trans. 1999 1113
28. A. Dervisi, P.G. Edwards, P.D. Newman, and R.P. Tooze J. Chem. Soc., Dalton Trans. 2000 523
29. L. Crawford, D.J. Cole-Hamilton, and M. Bühl Organometallics 2015
30. G.M. Strunz Studies in Natural Products Chemistry Vol. 24 2000 Elsevier 683 Part E
31. H. Cho, J.M. Beale, C. Graff, U. Mocek, A. Nakagawa, S. Omura, and H.G. Floss J. Am. Chem. Soc. 115 1993 12296
32. F.L. Buchholz Ullmann's Encyclopedia of Industrial Chemistry 2000 Wiley-VCH Verlag GmbH & Co. KGaA
33. B. El Ali, A. El-Ghanam, M. Fettouhi, and J. Tijani Tetrahedron Lett. 41 2000 5761
34. S.M. Shakil Hussain, R. Suleiman, and B. Ali Tetrahedron Lett. 53 2012 6535
35. U. Matteoli, A. Scrivanti, and V. Beghetto J. Mol. Catal. A: Chem. 213 2004 183
36. Y. Li, H. Alper, and Z. Yu Org. Lett. 8 2006 5199
37. H. Liu, G.P.S. Lau, and P.J. Dyson J. Org. Chem. 80 2015 386
38. B. Gabriele, G. Salerno, and M. Costa Catalytic Carbonylation Reactions Vol. 18 2006 Springer Berlin Heidelberg 239
39. J. Tsuji, M. Takahashi, and T. Takahashi Tetrahedron Lett. 21 1980 849
40. Y. Sakurai, S. Sakaguchi, and Y. Ishii Tetrahedron Lett. 40 1999 1701
41. S.T. Gadge, and B.M. Bhanage Synlett 2013 981
42. R.F. Heck J. Am. Chem. Soc. 94 1972 2712
43. H. Alper, B. Despeyroux, and J.B. Woell Tetrahedron Lett. 24 1983 5691
44. B. Gabriele, M. Costa, G. Salerno, and G.P. Chiusoli J. Chem. Soc., Perkin Trans. 1 1994 83
45. B. Gabriele, L. Veltri, G. Salerno, M. Costa, and Gian P. Chiusoli Eur. J. Org. Chem. 2003 1722
46. B. Gabriele, G. Salerno, L. Veltri, and M. Costa J. Organomet. Chem. 622 2001 84
47. S.T. Gadge, M.V. Khedkar, S.R. Lanke, and B.M. Bhanage Adv. Synth. Catal. 354 2012 2049
48. T.F. Murray, and J.R. Norton J. Am. Chem. Soc. 101 1979 4107
49. T.F. Murray, E.G. Samsel, V. Varma, and J.R. Norton J. Am. Chem. Soc. 103 1981 7520
50. B. El Ali, and H. Alper J. Org. Chem. 56 1991 5357
51. W.-Y. Yu, and H. Alper J. Org. Chem. 62 1997 5684
52. K. Kato, S. Motodate, T. Mochida, T. Kobayashi, and H. Akita Angew. Chem., Int. Ed. 48 2009 3326
53. B. Gabriele, R. Mancuso, V. Maltese, L. Veltri, and G. Salerno J. Org. Chem. 77 2012 8657
54. B. Gabriele, L. Veltri, R. Mancuso, G. Salerno, and M. Costa Eur. J. Org. Chem. 2012 2549
55. T. Kusakabe, K. Kawaguchi, M. Kawamura, N. Niimura, R. Shen, H. Takayama, and K. Kato Molecules 17 2012 9220
56. T. Kusakabe, Y. Kawai, R. Shen, T. Mochida, and K. Kato Org. Biomol. Chem. 10 2012 3192
57. T. Kusakabe, H. Sagae, and K. Kato Org. Biomol. Chem. 11 2013 4943
58. R. Shen, T. Kusakabe, K. Takahashi, and K. Kato Org. Biomol. Chem. 12 2014 4602
59. T. Kusakabe, T. Takahashi, R. Shen, A. Ikeda, Y.D. Dhage, Y. Kanno, Y. Inouye, H. Sasai, T. Mochida, and K. Kato Angew. Chem., Int. Ed. 52 2013 7845
60. M. Vilches-Herrera, L. Domke, and A. Börner ACS Catal. 4 2014 1706
61. R. Franke, D. Selent, and A. Börner Chem. Rev. 112 2012 5675
62. J. Pospech, I. Fleischer, R. Franke, S. Buchholz, and M. Beller Angew. Chem., Int. Ed. 52 2013 2852
63. Y. Ishii, K. Miyashita, K. Kamita, and M. Hidai J. Am. Chem. Soc. 119 1997 6448
64. X.J. Fang, M. Zhang, R. Jackstell, and M. Beller Angew. Chem., Int. Ed. 52 2013 4645
65. X.J. Fang, R. Jackstell, and M. Beller Chem. Eur. J. 20 2014 7939
66. T. Kobayashi, and M. Tanaka J. Chem. Soc., Chem. Commun. 1981 333
67. R. Grigg, and S.P. Mutton Tetrahedron 66 2010 5515
68. X.-F. Wu, H. Neumann, and M. Beller Chem. Soc. Rev. 40 2011 4986
69. R. Chinchilla, and C. Nájera Chem. Rev. 107 2007 874
70. K.T. Neumann, S.R. Laursen, A.T. Lindhardt, B. Bang-Andersen, and T. Skrydstrup Org. Lett. 16 2014 2216
71. L.A. Aronica, A.M. Caporusso, G. Tuci, C. Evangelisti, M. Manzoli, M. Botavina, and G. Martra Appl. Catal., A 480 2014 1
72. M. Genelot, V. Dufaud, and L. Djakovitch Adv. Synth. Catal. 355 2013 2604
73. X.-F. Wu, H. Neumann, and M. Beller Angew. Chem., Int. Ed. 50 2011 11142
74. S. Zhang, L. Wang, X. Feng, and M. Bao Org. Biomol. Chem. 12 2014 7233
75. F. Zeng, and H. Alper Org. Lett. 15 2013 2034
76. I.U. Khand, G.R. Knox, P.L. Pauson, and W.E. Watts J. Chem. Soc., Perkin Trans. 1973 975
77. N. Jeong P. Knochel, B.A. Molander, Comprehensive Organic Synthesis II 2014 Elsevier Amsterdam 1106
78. H.-W. Lee, and F.-Y. Kwong Eur. J. Org. Chem. 2010 789
79. J.G. Donkervoort, A.R. Gordon, C. Johnstone, J.W. Kerr, and U. Lange Tetrahedron 52 1996 7391
80. N.E. Schore, and M.C. Croudace J. Org. Chem. 46 1981 5436
81. N. Jeong, S.H. Hwang, Y. Lee, and Y.K. Chung J. Am. Chem. Soc. 116 1994 3159
82. B.Y. Lee, Y.K. Chung, N. Jeong, Y. Lee, and S.H. Hwang J. Am. Chem. Soc. 116 1994 8793
83. N.Y. Lee, and Y.K. Chung Tetrahedron Lett. 37 1996 3145
84. B.L. Pagenkopf, and T. Livinghouse J. Am. Chem. Soc. 118 1996 2285
85. D.B. Belanger, and T. Livinghouse Tetrahedron Lett. 39 1998 7641
86. J.W. Kim, and Y.K. Chung Synthesis 1998 142
87. T. Sugihara, and M. Yamaguchi J. Am. Chem. Soc. 120 1998 10782
88. Y. Wang, L. Xu, R. Yu, J. Chen, and Z. Yang Chem. Commun. 2012 8183
89. C. Exon, and P. Magnus J. Am. Chem. Soc. 105 1983 2477
90. J. Castro, A. Moyano, M.A. Pericàs, A. Riera, A.E. Greene, A. Alvarez-Larena, and J.F. Piniella J. Org. Chem. 61 1996 9016
91. J. Castro, H. Sorensen, A. Riera, C. Morin, A. Moyano, M.A. Pericas, and A.E. Greene J. Am. Chem. Soc. 112 1990 9388
92. K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe Tetrahedron Lett. 41 2000 891
93. K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe Tetrahedron: Asymmetry 11 2000 797
94. S.J. Sturla, and S.L. Buchwald J. Org. Chem. 67 2002 3398
95. T.M. Schmid, and G. Consiglio Tetrahedron: Asymmetry 15 2004 2205
96. T.M. Schmid, S. Gischig, and G. Consiglio Chirality 17 2005 353
97. P. Magnus, and L.M. Principe Tetrahedron Lett. 26 1985 4851
98. C. Mukai, T. Yoshida, M. Sorimachi, and A. Odani Org. Lett. 8 2005 83
99. Y. Higuchi, S. Higashimae, T. Tamai, and A. Ogawa Tetrahedron 69 2013 11197
100. E.R.H. Jones, T.Y. Shen, and M.C. Whiting J. Chem. Soc. 1950 230
101. E.R.H. Jones, T.Y. Shen, and M.C. Whiting J. Chem. Soc. 1951 48
102. E.R.H. Jones, G.H. Whitman, and M.C. Whiting J. Chem. Soc. 1865 1954
103. R.W. Rosenthal, and L.H. Schwartman J. Org. Chem. 24 1959 836
104. R.W. Rosenthal, L.H. Schwartman, N.P. Greco, and R. Proper J. Org. Chem. 28 1963 2835
105. H. Alper, and I. Amer J. Mol. Catal. 54 1989 L33
106. N. Satyanarayana, and H. Alper Organometallics 10 1991 804
107. H. Arzoumanian, F. Cochini, D. Nuel, and N. Rosas Organometallics 1993 1871 12
108. H. Arzoumanian, F. Cochini, D. Nuel, J.F. Petrignani, and N. Rosas Organometallics 11 1992 493
109. H. Arzoumanian, M. Jean, D. Nuel, A. Cabrera, J.L.G. Gutierrez, and N. Rosas Organometallics 14 1995 5438
110. G.P. Chiusoli, and L. Cassar Angew. Chem., Int. Ed. 6 1967 124
111. L. Pagès, A. Llebaría, F. Camps, E. Molins, C. Miravitlles, and J.M. Moretó J. Am. Chem. Soc. 114 1992 10449
112. G. Garcia-Gómez, and J.M. Moretó Chem. Eur. J. 7 2001 1503
113. F. Camps, J. Coll, J.M. Moreto, and J. Torras J. Org. Chem. 1989 1969 54
114. F. Camps, J.M. Moreto, and L. Pages Tetrahedron 48 1992 3147
115. D. Del-Moral, S. Ricart, and J.M. Moretó Chem. Eur. J. 16 2010 9193
116. Y. Hoshimoto, T. Ohata, Y. Sasaoka, M. Ohashi, and S. Ogoshi J. Am. Chem. Soc. 136 2014 15877
117. T. Kondo, N. Suzuki, T. Okada, and T. Mitsudo J. Am. Chem. Soc. 119 1997 6187
118. T. Morimoto, N. Chatani, Y. Fukumoto, and S. Murai J. Org. Chem. 62 1997 3762
119. K. Itami, K. Mitsudo, and J.-I. Yoshida Angew. Chem., Int. Ed. 41 2002 3481
120. N. Chatani, T. Morimoto, Y. Fukumoto, and S. Murai J. Am. Chem. Soc. 120 1998 5335
121. Q. Huang, and R. Hua Catal. Commun. 8 2007 1031
122. T. Kondo, Y. Kaneko, Y. Taguchi, A. Nakamura, T. Okada, M. Shiotsuki, Y. Ura, K. Wada, and T.-A. Mitsudo J. Am. Chem. Soc. 124 2002 6824
123. T. Fukuyama, Y. Higashibeppu, R. Yamaura, and I. Ryu Org. Lett. 9 2007 587
124. N. Chatani, T. Morimoto, A. Kamitani, Y. Fukumoto, and S. Murai J. Organomet. Chem. 579 1999 177
125. T. Kondo, M. Nomura, Y. Ura, K. Wada, and T.-A. Mitsudo J. Am. Chem. Soc. 128 2006 14816
126. N. Chatani, Y. Fukumoto, T. Ida, and S. Murai J. Am. Chem. Soc. 115 1993 11614
127. N. Suzuki, T. Kondo, and T. Mitsudo Organometallics 17 1998 766
128. T. Mise, P. Hong, and H. Yamazaki J. Org. Chem. 48 1983 238
129. S. Inoue, K. Yokota, H. Tatamidani, Y. Fukumoto, and N. Chatani Org. Lett. 8 2006 2519
130. F. Ziyanak, M. Kuş, and L. Artok Adv. Synth. Catal. 353 2011 897
131. N. Jeong Organometallics 17 1998 3642
132. T. Kobayashi, Y. Koga, and K. Narasaka J. Organomet. Chem. 624 2001 73
133. F. Chahdoura, L. Dubrulle, K. Fourmy, J. Durand, D. Madec, and M. Gómez Eur. J. Inorg. Chem. 2013 5138
134. Y. Hayashi, K. Ogawa, F. Inagaki, and C. Mukai Org. Biomol. Chem. 10 2012 4747
135. T. Saito, K. Sugizaki, T. Otani, and T. Suyama Org. Lett. 9 2007 1239
136. P.A. Wender, N.M. Deschamps, and G.G. Gamber Angew. Chem., Int. Ed. 2003 1853 42
137. B.L. Lu, Y. Wei, and M. Shi Organometallics 31 2012 4601
138. G.-Q. Chen, and M. Shi Chem. Commun. 2013 698
139. P.A. Evans, A.J. Burnie, and D.E. Negru Org. Lett. 16 2014 4356
140. N. Jeong, B.K. Sung, and Y.K. Choi J. Am. Chem. Soc. 122 2000 6771
141. B.-M. Fan, J.-H. Xie, S. Li, Y.-Q. Tu, and Q.-L. Zhou Adv. Synth. Catal. 347 2005 759
142. W. Chen, J.-H. Tay, J. Ying, M. Sabat, X.-Q. Yu, and L. Pu Chem. Commun. 2013 170
143. X. Li, S. Huang, C.M. Schienebeck, D. Shu, and W. Tang Org. Lett. 14 2012 1584
144. T. Fukuyama, Y. Ohta, C. Brancour, K. Miyagawa, I. Ryu, A.L. Dhimane, L. Fensterbank, and M. Malacria Chem. Eur. J. 18 2012 7243
145. S.-W. Zhang J. Mol. Catal. A: Chem. 143 1999 211
146. E. Yoneda, T. Kaneko, S.-W. Zhang, K. Onitsuka, and S. Takahashi Tetrahedron Lett. 40 1999 7811
147. K. Fuji, T. Morimoto, K. Tsutsumi, and K. Kakiuchi Chem. Commun. 2005 3295
148. Q. Huang, and R. Hua Chem. Eur. J. 15 2009 3817
149. S. Inoue, Y. Fukumoto, and N. Chatani J. Org. Chem. 72 2007 6588
150. T. Morimoto, K. Yamasaki, A. Hirano, K. Tsutsumi, N. Kagawa, K. Kakiuchi, Y. Harada, Y. Fukumoto, N. Chatani, and T. Nishioka Org. Lett. 11 2009 1777
151. L. Artok, M. Kuş, Ö. AksIn-Artok, F.N. Dege, and F.Y. ÖzkIlInç Tetrahedron 65 2009 9125
152. J. Dheur, M. Sauthier, Y. Castanet, and A. Mortreux Adv. Synth. Catal. 349 2007 2499
153. C. Wang, T. Morimoto, H. Kanashiro, H. Tanimoto, Y. Nishiyama, K. Kakiuchi, and L. Artok Synlett 2014 1155
154. Q. Huang, and R. Hua Chem. Eur. J. 13 2007 8333
155. H. Klein, R. Jackstell, T. Netscher, W. Bonrath, and M. Beller ChemCatChem 3 2011 1273
156. K. Doyama, T. Joh, S. Takahashi, and T. Shiohara Tetrahedron Lett. 27 1986 4497
157. E.M. Campi, and W.R. Jackson Aust. J. Chem. 42 1989 471
158. B.G.V.d. Hoven, and H. Alper J. Org. Chem. 64 1999 3964
159. I. Ojima, P. Ingallina, R.J. Donovan, and N. Clos Organometallics 10 1991 38
160. Laura A. Aronica, S. Terreni, Anna M. Caporusso, and P. Salvadori Eur. J. Org. Chem. 2001 4321
161. P. Eilbracht, C. Hollmann, Axel M. Schmidt, and L. Bärfacker Eur. J. Org. Chem. 2000 1131
162. J.R. Johnson, G.D. Cuny, and S.L. Buchwald Angew. Chem., Int. Ed. 34 1995 1760
163. V. Agabekov, W. Seiche, and B. Breit Chem. Sci. 4 2013 2418
164. P. Nanayakkara, and H. Alper Adv. Synth. Catal. 348 2006 545
165. E.B. Bauer Curr. Org. Chem. 12 2008 1341
166. W.M. Czaplik, M. Mayer, J. Cvengros, and A. Jacobi von Wangelin ChemSusChem 2 2009 396
167. C.-L. Sun, B.-J. Li, and Z.-J. Shi Chem. Rev. 111 2011 1293
168. A. Fürstner Angew. Chem., Int. Ed. 48 2009 1364
169. A. Correa Chem. Soc. Rev. 37 2008 1108
170. M.D. Greenhalgh, A.S. Jones, and S.P. Thomas ChemCatChem 7 2015 190
171. M. Beesu, and M. Periasamy J. Org. Chem. 76 2011 543
172. M. Periasamy, M. Beesu, and D. Shyam Raj J. Organomet. Chem. 693 2008 2843
173. M. Periasamy, A. Mukkanti, and D.S. Raj Organometallics 23 2004 6323
174. P. Mathur, R.K. Joshi, B. Jha, A.K. Singh, and S.M. Mobin J. Organomet. Chem. 695 2010 2687
175. K.M. Driller, H. Klein, R. Jackstell, and M. Beller Angew. Chem., Int. Ed. 48 2009 6041
176. S. Prateeptongkum, K.M. Driller, R. Jackstell, A. Spannenberg, and M. Beller Chem. Eur. J. 16 2010 9606
177. S. Prateeptongkum, K.M. Driller, R. Jackstell, and M. Beller Chem. Asian J. 5 2010 2173
178. K.M. Driller, S. Prateeptongkum, R. Jackstell, and M. Beller Angew. Chem., Int. Ed. 50 2011 537
179. M. Pizzetti, A. Russo, and E. Petricci Chem. Eur. J. 17 2011 4523
180. M. Periasamy, C. Rameshkumar, and A. Mukkanti J. Organomet. Chem. 649 2002 209
181. M. Jegelka, and B. Plietker Iron Catalysis Vol. 33 2011 Springer Berlin Heidelberg 177
182. W. Hieber, F. Sonnekalb, and E. Becker Chem. Ber. 63 1930 973
183. N. Rosas, P. Sharma, I. Arellano, M. Ramírez, D. Pérez, S. Hernández, and A. Cabrera Organometallics 24 2005 4893
184. F.A. Hicks, N.M. Kablaoui, and S.L. Buchwald J. Am. Chem. Soc. 118 1996 9450
185. F.A. Hicks, N.M. Kablaoui, and S.L. Buchwald J. Am. Chem. Soc. 121 1999 5881
186. F.A. Hicks, and S.L. Buchwald J. Am. Chem. Soc. 118 1996 11688
187. F.A. Hicks, and S.L. Buchwald J. Am. Chem. Soc. 121 1999 7026
188. T. Shibata, and K. Takagi J. Am. Chem. Soc. 122 2000 9852
189. T. Shibata, N. Toshida, M. Yamasaki, S. Maekawa, and K. Takagi Tetrahedron 61 2005 9974
190. N. Jeong, D.H. Kim, and J.H. Choi Chem. Commun. 2004 1134
191. T. Shibata, S. Kadowaki, M. Hirase, and K. Takagi Synlett 2003 0573
192. T. Shibata, K. Yamashita, H. Ishida, and K. Takagi Org. Let. 3 2001 1217
193. E. Negishi, S.J. Holmes, J.M. Tour, and J.A. Miller J. Am. Chem. Soc. 107 1985 2568
194. F. Goettmann, P. Le Floch, and C. Sanchez Chem. Commun. 2006 180
195. Y. Uenoyama, T. Fukuyama, O. Nobuta, H. Matsubara, and I. Ryu Angew. Chem., Int. Ed. 44 2005 1075
196. I. Ryu, K. Matsu, S. Minakata, and M. Komatsu J. Am. Chem. Soc. 120 1998 5838
197. I. Ryu, H. Miyazato, H. Kuriyama, K. Matsu, M. Tojino, T. Fukuyama, S. Minakata, and M. Komatsu J. Am. Chem. Soc. 125 2003 5632
198. I. Ryu, T. Fukuyama, M. Tojino, Y. Uenoyama, Y. Yonamine, N. Terasoma, and H. Matsubara Org. Biomol. Chem. 9 2011 3780