Recent developments in palladium-catalyzed formation of five- and six-membered fused heterocycles

Synthesis

Volumn 44, Issue 6, 2012, Pages 817-847

  Majumdar, K C ^a,b   Samanta, Srikanta ^a   Sinha, Biswajit ^a  

^a UNIVERSITY OF KALYANI   (India)

^b TEZPUR UNIVERSITY   (India)

Author keywords

C C coupling; C H activation; fused heterocycles; palladium catalysis; regioselectivity; stereoselectivity

Indexed keywords

ARYL HALIDES; ARYL TRIFLATES; C-C COUPLING; C-H ACTIVATION; CYCLIZATION REACTIONS; CYCLIZATIONS; FUNCTIONALIZATIONS; HECK REACTIONS; HETEROCYCLES; HETEROCYCLIC COMPOUND; HETEROCYCLIC RINGS; INTERNAL ALKYNES; INTRAMOLECULAR ANNULATION; INTRAMOLECULAR CYCLIZATIONS; MULTI-STEP; NATURAL PRODUCTS; PALLADIUM CATALYSIS; PALLADIUM-CATALYZED; STEREOSELECTIVE SYNTHESIS; TERMINAL ALKYNE; VINYLIC HALIDES;

ACETYLENE; ACTIVATION ANALYSIS; CATALYSIS; COUPLINGS; OLEFINS; ORGANIC COMPOUNDS; PARAFFINS; REGIOSELECTIVITY; STEREOCHEMISTRY; STEREOSELECTIVITY;

CYCLIZATION;

ALKANE DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; ALLENE DERIVATIVE; ARYL HALOGENIDE; ARYL TRIFLATE; FUSED HETEROCYCLIC RINGS; HALIDE; PALLADIUM; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; VINYLIC HALIDE;

AMINATION; ANNULATION REACTION; BIARYL COUPLING; CARBONYLATION; CATALYSIS; CHEMICAL COMPOSITION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HECK REACTION; HYDROXYLATION; MOLECULAR INTERACTION; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

EID: 84858080531     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289734     Document Type: Review

References (359)

1. Eicher T, Hauptmann S, The Chemistry of Heterocycles: Structure, Reactions, Synthesis and Applications Wiley-VCH Weinheim 2003
2. For a special issue, see: Chem. Rev. 2004 104 Issue 5
3. Kang E J., Lee E, Chem. Rev. 2005 105 4348
4. Saleem M, Kim H J., Ali M S., Lee Y S., Nat. Prod. Rep. 2005 22 696
5. Bermejo A, Figadere B, Zafra-Polo M.-C, Barrachina I, Estornell E, Cortes D, Nat. Prod. Rep. 2005 22 269
6. Daly J W., Spande T F., Garraffo H M., J. Nat. Prod. 2005 68 1556
7. Yamamoto Y, Gridnev I D., Patil N T., Jin T, Chem. Commun. 2009 5075
8. Nakamura I, Yamamoto Y, Chem. Rev. 2004 104 2127
9. Rodríguez F, Fananas F J., In Targets in Heterocyclic Systems Vol. 13 Attanasi O A. Spinelli D Royal Society of Chemistry London 2009 273
10. Beletskaya I P., Cheprakov A V., Chem. Rev. 2000 100 3009
11. Poupaert J, Carato P, Colacino E, Yous S, Curr. Med. Chem. 2005 12 877
12. Conney A H., Burns J J., J. Pharmacol. Exp. Ther. 1960 128 340
13. Wei H, Yang G.-F, Bioorg. Med. Chem. 2006 14 8280
14. Kato-Noguchi H, Macias F A., Molinillo J M. G., J. Plant Physiol. 2010 167 1221
15. Barber A, Bender H M., Gottschlich R, Greiner H E., Harting J, Mauler F, Seyfried C A., Meth. Find. Exp. Clin. Pharmacol. 1999 21 105
16. Venugopal V, Naidu V G., Prasad P R., Pestology 2003 27 29
17. Zhang P, Terefenko E A., Wrobel J, Zhang Z, Zhu Y, Cohen J, Marschke K B., Mais D, Bioorg. Med. Chem. Lett. 2001 11 2747
18. Tsuji J, Palladium Reagents and Catalysts: Innovations in Organic Synthesis Wiley and Sons New York 1995
19. Li J J., Gribble G W., Palladium in Heterocyclic Chemistry Pergamon New York 2000
20. Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 2 Negishi E de Meijere A John Wiley & Sons New York 2002 2309
21. Tsuji J, Palladium Reagents and Catalysts: New Perspectives for the 21st Century Wiley and Sons New York 2003
22. Palladium in Organic Synthesis Tsuji J Springer Berlin 2005
23. Stahl S S., Angew. Chem. Int. Ed. 2004 43 3400
24. Zeni G, Larock R C., Chem. Rev. 2004 104 2285
25. Muzart J, Tetrahedron 2005 61 5955
26. Muzart J, Tetrahedron 2005 61 9423
27. Cacchi S, Fabrizi G, Chem. Rev. 2005 105 2873
28. Phan N T. S., Van Der Sluys M, Jones C W., Adv. Synth. Catal. 2006 348 609
29. Zeni G, Larock R C., Chem. Rev. 2006 106 4644
30. Humphrey G R., Kuethe J T., Chem. Rev. 2006 106 2875
31. Patil S, Buolamwini J K., Curr. Org. Synth. 2006 3 477
32. Ackermann L, Synlett 2007 507
33. Alberico D, Scott M E., Lautens M, Chem. Rev. 2007 107 174
34. Krüger (née Alex) K, Tillack A, Beller M, Adv. Synth. Catal. 2008 350 2153
35. Patil S A., Patil R, Miller D D., Curr. Med. Chem. 2009 16 2531
36. Majumdar K C., Debnath P, Roy B, Heterocycles 2009 78 2661
37. Majumdar K C., Roy B, Debnath P, Taher A, Curr. Org. Chem. 2010 14 846
38. Majumdar K C., Chattopadhyay B, Maji P, Chattopadhyay S K., Samanta S, Heterocycles 2010 81 517
39. Majumdar K C., Chattopadhyay B, Maji P, Chattopadhyay S K., Samanta S, Heterocycles 2010 81 795
40. Majumdar K C., Debnath P, De N, Curr. Org. Chem. 2011 15 1760
41. Tietze L F., Beifuss U, Angew. Chem., Int. Ed. Engl. 1993 32 131
42. de Meijere A, Meyer F E., Angew. Chem., Int. Ed. Engl. 1995 33 2379
43. Tietze L F., Lieb M, Curr. Opin. Chem. Biol. 1998 2 363
44. Tietze L F., Haunert F, In Stimulating Concepts in Chemistry Vögtle F Stoddart J F. Shibasaki M Wiley-VCH Weinheim 2000 39
45. Tietze L F., Modi A, Med. Res. Rev. 2000 20 304
46. Trost B M., Acc. Chem. Res. 2002 35 695
47. Cuny G, Bois-Choussy M, Zhu J, Angew. Chem. Int. Ed. 2003 42 4774
48. de Meijere A, Von Zezschwitz P, Bräse S, Acc. Chem. Res. 2005 38 413
49. Ackermann L, Althammer A, Angew. Chem. Int. Ed. 2007 46 1627
50. Nandi S, Ray J K., Tetrahedron Lett. 2009 50 6993
51. Jana R, Samanta S, Ray J K., Tetrahedron Lett. 2008 49 851
52. For intramolecular C-arylation of imidazole and pyrrole, see:, Arai N, Takahashi M, Mitani M, Mori A, Synlett 2006 3170
53. Dandepally S R., Williams A L., Tetrahedron Lett. 2009 50 1395
54. Maruyama J, Yamashita H, Watanabe T, Arai S, Nishida A, Tetrahedron 2009 65 1327
55. Mao H, Wan J.-P, Pan Y, Sun C, Tetrahedron Lett. 2010 51 1844
56. Majumdar K C., Chakravorty S, Shyam P K., Taher A, Synthesis 2009 403
57. Weinrich M L., Beck H P., Tetrahedron Lett. 2009 50 6968
58. Kaim L E., Gizzi M, Grimaud L, Org. Lett. 2008 10 3417
59. Phakhodee W, Ploypradith P, Sahakitpichan P, Ruchirawat S, Tetrahedron 2009 65 351
60. Rene O, Lapointe D, Fagnou K, Org. Lett. 2009 11 4560
61. Kim H S., Lee H S., Kim S H., Kim J N., Tetrahedron Lett. 2009 50 3154
62. Harayama H, Kuroki T, Kimura M, Tanaka S, Tamaru Y, Angew. Chem. Int. Ed. 1997 36 2352
63. Kim H S., Gowrisankar S, Kim E S., Kim J N., Tetrahedron Lett. 2008 49 6569
64. de Meijere A, Diederich F, Metal-Catalyzed Cross-Coupling Reactions Vols. 1 and 2 Wiley-VCH Weinheim 2004
65. Dyker G, Handbook of C - H Transformations Vol. 1 Wiley-VCH Weinheim 2005
66. Dyker G, Angew. Chem. Int. Ed. 1999 38 1698
67. Ohno H, Yamamoto M, Iuchi M, Tanaka T, Angew. Chem. Int. Ed. 2005 44 5103
68. Pinto A, Neuville L, Zhu J, Angew. Chem. Int. Ed. 2007 46 3291
69. Ruck R T., Huffman M A., Kim M M., Shevlin M, Kandur W V., Davies I W., Angew. Chem. Int. Ed. 2008 47 4711
70. Huang Q, Larock R C., Tetrahedron Lett. 2009 50 7235
71. Lu Z, Hu C, Guo J, Li J, Cui Y, Jia Y, Org. Lett. 2010 12 480
72. Majumdar K C., Chakravorty S, Ray K, Synthesis 2008 2991
73. Majumdar K C., Sinha B, Maji P K., Chattopadhyay S, Tetrahedron 2009 65 2751
74. Stoll A, Hofmann A, In The Alkaloids Vol. 8 Manske R H. F. Holmes H L. Academic Press New York 1965 725
75. Stadler P A., Stutz P, In The Alkaloids Vol. 15 Manske R H. F. Holmes H L. Academic Press New York 1975 1
76. Groger D, Floss H G., In The Alkaloids Vol. 50 Cordell G A. Academic Press New York 1990 171
77. Kurokawa T, Isomura M, Tokuyama H, Fukuyama T, Synlett 2009 775
78. Wolfe J P., Rennels R A., Buchwald S L., Tetrahedron 1996 52 7525
79. Lee K L., Goh J B., Martin S F., Tetrahedron Lett. 2001 42 1635
80. Dai W.-M, Shi J, Wu J, Synlett 2008 2716
81. Dounay A B., Humphreys P G., Overman L E., Wrobleski A D., J. Am. Chem. Soc. 2008 130 5368
82. Alonso F, Rodríguez-Fernández M, Sánchez D, Yus M, Synthesis 2010 3013
83. Chen H, Tan R X., Liu Z L., Zhang Y, J. Nat. Prod. 1996 59 668
84. de la Torre M C., Rodríguez B, Bruno B, Vassallo N, Bondì M L., Piozzi F, Servettaz O, J. Nat. Prod. 1997 60 1229
85. Rodríguez B, de la Torre M C., Jimeno M.-L, Bruno M, Vassallo N, Bondì M L., Piozzi F, Servettaz O, J. Nat. Prod. 1997 60 348
86. Malakov P Y., Papanov G Y., Phytochemistry 1998 49 2449
87. Alonso F, Sánchez D, Yus M, Adv. Synth. Catal. 2008 350 2118
88. Chen W.-H, Pang Y, Tetrahedron Lett. 2009 50 6680
89. Perron F, Albizati K F., Chem. Rev. 1989 89 1617
90. Barrett A G. M., Pena M, Aillardsen J A., J. Org. Chem. 1996 61 1082
91. Kool E T., Acc. Chem. Res. 2002 35 936
92. Wu Q, Simons C, Synthesis 2004 1533
93. Denmark S E., Regens C S., Kobayashi T, J. Am. Chem. Soc. 2007 129 2774
94. Awasaguchi K, Miyazawa M, Uoya I, Inoue K, Nakamura K, Yokoyama H, Kakuda H, Hirai Y, Synlett 2010 2392
95. Zhang Z, Zhang J, Tan J, Wang Z, J. Org. Chem. 2008 73 5180
96. Majumdar K C., Samanta S, Nandi R K., Chattopadhyay B, Tetrahedron Lett. 2010 51 3807
97. Yip K.-T, Zhu N.-Y, Yang D, Org. Lett. 2009 11 1911
98. Söderberg B C., Shriver J A., J. Org. Chem. 1997 62 5838
99. Söderberg B C. G., Banini S R., Turner M R., Minter A R., Arrington A K., Synthesis 2008 903
100. Gorugantula S P., Carrero-Martínez G M., Dantale S W., Söderberg B C. G., Tetrahedron 2010 66 1800
101. Wallace J M., Söderberg B C. G., Tamariz J, Akhmedov N G., Tetrahedron 2008 64 9675
102. Arai S, Koike Y, Hada H, Nishida A, J. Am. Chem. Soc. 2010 132 4522
103. An G, Zhou W, Zhang G, Sun H, Han J, Pan Y, Org. Lett. 2010 12 4482
104. Liegault B, Fagnou K, Organometallics 2008 27 4841
105. Beccalli E M., Borsini E, Broggini G, Rigamonti M, Sottocornola S, Synlett 2008 1053
106. Sun L, Tran N, Tang F, App H, Hirth P, McMahon G, Tang C, J. Med. Chem. 1998 41 2588
107. Wood E R., Kuyper L, Petrov K G., Hunter R N. III., Harris P A., Lackey K, Bioorg. Med. Chem. Lett. 2004 14 953
108. Ueda S, Okada T, Nagasawa H, Chem. Commun. 2010 46 2462
109. Jaegli S, Vors J.-P, Neuville L, Zhu J, Synlett 2009 2997
110. Jaegli S, Dufour J, Wei H.-L, Piou T, Duan X.-H, Vors J.-P, Neuville L, Zhu J, Org. Lett. 2010 12 4498
111. Jaegli S, Vors J.-P, Neuville L, Zhu J, Tetrahedron 2010 66 8911
112. Campeau L.-C, Fagnou K, Chem. Commun. 2006 1253
113. Giri R, Shi B.-F, Engle K E., Maugel N, Yu J.-Q, Chem. Soc. Rev. 2009 38 3242
114. Jazzar R, Hitch J, Renaudat A, Sofack-Kreutzer J, Baudoin O, Chem. Eur. J. 2010 16 2654
115. Cuny G, Bois-Choussy M, Zhu J, J. Am. Chem. Soc. 2004 126 14475
116. Salcedo A, Neuville L, Rondot C, Retailleau P, Zhu J, Org. Lett. 2008 10 857
117. Rozhkov R V., Larock R C., J. Org. Chem. 2010 75 4131
118. Coy B E. D., Jovanovic L, Sefkow M, Org. Lett. 2010 12 1976
119. For reviews, see:, Prato M, Top. Curr. Chem. 1999 199 173
120. Diederich F, Gomez-Lopez M, Chem. Soc. Rev. 1999 28 263
121. See the special issue on functionalized fullerenes: J. Mater. Chem. 2002 12 1931-2159
122. Guldi D M., Zerbetto F, Georgakilas V, Prato M, Acc. Chem. Res. 2005 38 38
123. For reviews, see:, Jensen A W., Wilson S R., Schuster D I., Bioorg. Med. Chem. 1996 4 767
124. Bianco A, Da Ros T, Prato M, Toniolo C, J. Pept. Sci. 2001 7 208
125. Bosi S, Da Ros T, Spalluto G, Prato M, Eur. J. Med. Chem. 2003 38 913
126. Nakamura E, Isobe H, Acc. Chem. Res. 2003 36 807
127. Zhu B, Wang G.-W, J. Org. Chem. 2009 74 4426
128. Adachi S, Koike K, Takayanagi I, Pharmacology 1996 53 250
129. Kam T.-S, Subramaniam G, Lim K.-H, Choo Y.-M, Tetrahedron Lett. 2004 45 5995
130. Sunazuka T, Shirahata T, Tsuchiya S, Hirose T, Mori R, Harigaya Y, Kuwajima I, Omura S, Org. Lett. 2005 7 941
131. Zhu B, Wang G.-W, Org. Lett. 2009 11 4334
132. Röver S, Adams D. R, Bénardeau A, Bentley J. M, Bickerdike M. J, Bourson A, Cliffe I. A, Coassolo P, Davidson J. E. P, Dourish C. T, Hebeisen P, Kennett G. A, Knight A. R, Malcolm C. S, Mattei P, Misra A, Mizrahi J, Muller M, Porter R. H. P, Richter H, Taylor S, Vickers S. P, Bioorg. Med. Chem. Lett. 2005 15 3604
133. Goldberg D R., Choi Y, Cogan D, Corson M, DeLeon R, Gao A, Gruenbaum L, Hao M. H, Joseph D, Kashem M. A, Miller C, Moss N, Netherton M. R, Pargellis C. P, Pelletier J, Sellati R, Skow D, Torcellini C, Tseng Y.-C, Wang J, Wasti R, Werneburg B, Wu J. P, Xiong Z, Bioorg. Med. Chem. Lett. 2008 18 938
134. Trost B M., Dong G, J. Am. Chem. Soc. 2006 128 6054
135. Chen A, Sun X T., Tetrahedron Lett. 2007 48 3459
136. Laliberte S, Dornan P K., Chen A, Tetrahedron Lett. 2010 51 363
137. Yoshida M, Maeyama Y, Shishido K, Tetrahedron Lett. 2010 51 6008
138. Kapur A, Kumar K, Singh L, Singh P, Elango M, Subramanian V, Gupta V, Kanwal P, Ishar M P. S., Tetrahedron 2009 65 4593
139. West R, J. Org. Chem. 1958 23 1552
140. Ikegami S, Hamamoto H, Chem. Rev. 2009 109 583
141. Mennecke K, Cecilia R, Glasnov T N., Gruhl S, Vogt C, Feldhoff A, Vargas M A. L., Kappe C O., Kunz U, Kirschning A, Adv. Synth. Catal. 2008 350 717
142. Huang W, Liu J H.-C, Alayoglu P, Li Y, Witham C A., Tsung C.-K, Toste F D., Somorjai G A., J. Am. Chem. Soc. 2010 132 16771
143. For examples of palladium nanoparticles as catalysts in continuous-flow processes, see:, Hou Z, Theyssen N, Brinkmann A, Leitner W, Angew. Chem. Int. Ed. 2005 44 1346
144. Nikbin N, Ladlow M, Ley S V., Org. Process Res. Dev. 2007 11 458
145. For recent advances in the palladium-catalyzed synthesis of benzofuran derivatives, see:, Nakamura I, Mizushima Y, Yamagishi U, Yamamoto Y, Tetrahedron 2007 63 8670
146. Rasool N, Rashid M A., Reinke H, Fischer C, Langer P, Tetrahedron 2007 63 11626
147. Sakai N, Uchida N, Konakahara T, Tetrahedron Lett. 2008 49 3437
148. Fiandanese V, Bottalico D, Marchese G, Punzi A, Tetrahedron 2008 64 53
149. Huang X.-C, Liu Y L., Liang Y, Pi S.-F, Wang F, Li J.-H, Org. Lett. 2008 10 1525
150. Zhao L, Cheng G, Hu Y, Tetrahedron Lett. 2008 49 7364
151. Liang Y, Tao L.-M, Zhang Y.-H, Li J.-H, Synthesis 2008 3988
152. Faragó J, Kotschy A, Synthesis 2009 85
153. Zhao M Q., Crooks R M., Angew. Chem. Int. Ed. 1999 38 364
154. Huang W Y., Kuhn J N., Tsung C.-K, Zhang Y, Habas S E., Yang P, Somorjai G A., Nano Lett. 2008 8 2027
155. Söderberg B C. G., Gorugantula S P., Howerton C R., Petersen J L., Dantale S W., Tetrahedron 2009 65 7357
156. Cacchi S, Fabrizi G, Goggiamani A, Perboni A, Sferrazza A, Stabile P, Org. Lett. 2010 12 3279
157. Arcadi A, Cianci R, Ferrera G, Marinelli F, Tetrahedron 2010 66 2378
158. Konno T, Chae J, Ishihara T, Yamanaka H, J. Org. Chem. 2004 69 8258
159. Chae J, Konno T, Ishihara T, Yamanaka H, Chem. Lett. 2004 33 314
160. Fukuda Y, Furuta H, Kusama Y, Ebisu H, Oomori Y, Terashima S, J. Med. Chem. 1999 42 1448
161. Akanmu M A., Songkram C, Kagechika H, Honda K, Neurosci. Lett. 2004 364 199
162. Chen Z, Zhu J, Xie H, Li S, Wu Y, Gong Y, Synlett 2010 1418
163. Cationic palladium(II)-catalyzed addition reactions of arylboronic acids to carbon-heteroatom bonds, see:, Liu G, Lu X, J. Am. Chem. Soc. 2006 128 16504
164. Zhao B, Lu X, Org. Lett. 2006 8 5987
165. Dai H, Lu X, Org. Lett. 2007 9 3077
166. Lin S, Lu X, J. Org. Chem. 2007 72 9757
167. Yang M, Zhang X, Lu X, Org. Lett. 2007 9 5131
168. Song J, Shen Q, Xu F, Lu X, Org. Lett. 2007 9 2947
169. Yu X, Lu X, Org. Lett. 2009 11 4366
170. Han X, Lu X, Org. Lett. 2010 12 108
171. Han X, Lu X, Org. Lett. 2010 12 3336
172. Kim I, Kim K, Org. Lett. 2010 12 2500
173. Dai G, Larock R C., J. Org. Chem. 2003 68 920
174. Bossharth E, Desbordes P, Monteiro N, Balme G, Org. Lett. 2003 5 2441
175. Hu Y, Nawoschik K J., Liao Y, Ma J, Fathi R, Yang Z, J. Org. Chem. 2004 69 2235
176. Cacchi S, Fabrizi G, Goggiamani A, Adv. Synth. Catal. 2006 348 1301
177. Overman L E., Pennington L D., J. Org. Chem. 2003 68 7143
178. Kirsch S F., Binder J T., Liébert C, Menz H, Angew. Chem. Int. Ed. 2006 45 5878
179. Chernyak D, Skontos C, Gevorgyan V, Org. Lett. 2010 12 3242
180. Jeffery T, J. Chem. Soc., Chem. Commun. 1984 1287
181. Seregin I V., Gevorgyan V, J. Am. Chem. Soc. 2006 128 12050
182. Seregin I V., Schammel A W., Gevorgyan V, Org. Lett. 2007 9 3433
183. Seregin I V., Schammel A W., Gevorgyan V, Tetrahedron 2008 64 6876
184. Jiang T.-S, Tang R.-Y, Zhang X.-G, Li X.-H, Li J.-H, J. Org. Chem. 2009 74 8834
185. Bonadies F, Di Fabio R, Bonini C, J. Org. Chem. 1984 49 1647
186. Iwata N, Wang N, Yao X, Kitanaka S, J. Nat. Prod. 2004 67 1106
187. Morandim A A., Bergamo D C. B., Kato M J., Cavalheiro A J., Bolzani V S., Furlan M, Phytochem. Anal. 2005 16 282
188. Savitha G, Felix K, Perumal P T., Synlett 2009 2079
189. Lunt E, In Comprehensive Organic Chemistry Vol. 4 Barton D Ollis W D. Pergamon Press Oxford 1974 493
190. Sasaki T, Minamoto K, Sujuki T, Yamashita S, Tetrahedron 1980 36 865; and references cited therein
191. Marumoto R, Furukawa Y, Chem. Pharm. Bull. 1977 25 2974
192. Jones S A., Sayers J R., Walker R T., De Clercq E, J. Med. Chem. 1988 31 268
193. Macllwain C, Nature 1993 365 378
194. De Clercq E, J. Med. Chem. 1986 29 1561
195. Miyasaka T, Tanaka H, Baba M, Hayasaka H, Walker R T., Balzarini J, De Clercq E, J. Med. Chem. 1989 32 2507
196. Majumdar K C., Sinha B, Chattopadhyay B, Ray K, Tetrahedron Lett. 2008 49 4405
197. Roy S, Roy S, Neuenswander B, Hill D, Larock R C., J. Comb. Chem. 2009 11 1061
198. Nefzi A, Ostresh J M., Houghten R A., Chem. Rev. 1997 97 449
199. Ohno H, Okano A, Kosaka S, Tsukamoto K, Ohata M, Ishihara K, Maeda H, Tanaka T, Fujii N, Org. Lett. 2008 10 1171
200. Panteleev J, Geyer K, Aguilar-Aguilar A, Wang L, Lautens M, Org. Lett. 2010 12 5092
201. Selected examples of heteroaryl halides in direct arylation:, Zhang Y.-M, Razler T, Jackson P F., Tetrahedron Lett. 2002 43 8235
202. Masselot D, Charmant J P. H., Gallagher T, J. Am. Chem. Soc. 2006 128 694
203. Masuda N, Tanba S, Sugie A, Monguchi D, Koumura N, Hara K, Mori A, Org. Lett. 2009 11 2297
204. Huisgen R, Angew. Chem. 1963 75 604
205. Tornoe C W., Christensen C, Meldal M, J. Org. Chem. 2002 67 3057
206. Rostovtsev V V., Green L G., Fokin V V., Sharpless K B., Angew. Chem. Int. Ed. 2002 41 2596
207. Chernyak D, Gevorgyan V, Org. Lett. 2010 12 5558
208. Chen C.-C, Chin L.-Y, Yang S.-C, Wu M.-J, Org. Lett. 2010 12 5652
209. Schultz D M., Prescher J A., Kidd S, Marona-Lewicka D, Nichols D E., Monte A, Bioorg. Med. Chem. 2008 16 6242
210. Rizzo S, Riviere C, Piazzi L, Bisi A, Gobbi S, Bartolini M, Andrisano V, Morroni F, Tarozzi A, Monti J.-P, Rampa A, J. Med. Chem. 2008 51 2883
211. Kirilmis C, Ahmedzade M, Servi S, Koca M, Kizirgil A, Kazaz C, Eur. J. Med. Chem. 2008 43 300
212. Ando K, Kawamura Y, Akai Y, Kunitomo J, Yokomizo T, Yamashita M, Ohta S, Ohishi T, Ohishi Y, Org. Biomol. Chem. 2008 6 296
213. Gabriele B, Mancuso R, Salerno G, J. Org. Chem. 2008 73 7336
214. Watanabe K, Iwata Y, Adachi S, Nishikawa T, Yoshida Y, Kameda S, Ide M, Saikawa Y, Nakata M, J. Org. Chem. 2010 75 5573
215. Matsumoto N, Tsuchida T, Maruyama M, Kinoshita N, Homma Y, Iinuma H, Sawa T, Hamada M, Takeuchi T, Heida N, Yoshioka T, J. Antibiot. 1999 52 269
216. Matsumoto N, Tsuchida T, Nakamura H, Sawa R, Takahashi Y, Naganawa H, Iinuma H, Sawa T, Takeuchi T, Shiro M, J. Antibiot. 1999 52 276
217. Keivanloo A, Bakherad M, Rahimi A, Taheri S A. N., Tetrahedron Lett. 2010 51 2409
218. Keivanloo A, Bakherad M, Rahimi M, Synthesis 2010 1599
219. Larock R C., Babu S, Tetrahedron Lett. 1987 28 5291; and references therein
220. Mphahlele M J., Lesenyeho L G., Makelane H R., Tetrahedron 2010 66 6040
221. Jiao P.-F, Zhao B.-X, Wang W.-W, He Q.-X, Wan M.-S, Shin D.-S, Miao J.-Y, Bioorg. Med. Chem. Lett. 2006 16 2862
222. Touzeau F, Arrault A, Guillaumet G, Scalbert E, Pfeiffer B, Rettori M, Renard P, Merour J.-Y, J. Med. Chem. 2003 46 1962
223. Matsuoka H, Ohi N, Mihara M, Suzuki H, Miyamoto K, Maruyama N, Tsuji K, Kato N, Akimoto T, Takeda Y, Yano K, Kuroki T, J. Med. Chem. 1997 40 105
224. Kuroita T, Marubayashi N, Sano M, Kanzaki K, Inaba K, Kawakita T, Chem. Pharm. Bull. 1996 44 2051
225. Largeron M, Lockhart B, Pfeiffer B, Fleury M. B, J. Med. Chem. 1999 42 5043
226. Caliendo G, Grieco P, Perissutti E, Santagada V, Santini A, Albrizio S, Fattorusso C, Pinto A, Sorrentino R, Eur. J. Med. Chem. 1998 33 957
227. Sugimoto Y, Otani T, Oie S, Wierzba K, Yamada Y, J. Antibiot. 1990 43 417
228. Chowdhury C, Brahma K, Mukherjee S, Sasmal A K., Tetrahedron Lett. 2010 51 2859
229. Yoshida M, Higuchi M, Shishido K, Tetrahedron Lett. 2008 49 1678
230. For examples, see:, Ma W W., Kozlowski J F., McLaughlin J L., J. Nat. Prod. 1991 54 1153
231. Tyagi O D., Prasad A K., Wengel J, Boll P M., Olsen C E., Parmar V S., Sharma N K., Jha A, Bisht K S., Acta Chem. Scand. 1995 49 142
232. Lordello A L. L., Yoshida M, Phytochemistry 1997 46 741
233. Shi Z, Zhang C, Li S, Pan D, Ding S, Cui Y, Jiao N, Angew. Chem. 2009 121 4642
234. The palladium-catalyzed cocyclization of alkynes with 2-iodoanilines was reported by Larock and others:, Larock R C., Yum E K., Doty M J., Sham K K. C., J. Org. Chem. 1995 60 3270
235. Larock R C., Yum E K., Refvic M D., J. Org. Chem. 1998 63 765
236. Barluenga J, Rodríguez F, Fañanás F J., Chem. Asian J. 2009 4 1036
237. So C M., Yeung C C., Lau C P., Kwong F Y., J. Org. Chem. 2008 73 7803
238. Wassenaar J, van Zutphen S, Mora G, Le Floch P, Siegler M A., Spek A L., Reek J N. H., Organometallics 2009 28 2724
239. Lee H W., Lam F L., So C M., Lau S P., Chan A S. C., Kwong F Y., Angew. Chem. Int. Ed. 2009 48 7436
240. Kondoh A, Yorimitsu H, Oshima K, Org. Lett. 2010 12 1476
241. Kobayashi K, Hashimoto K, Fukamachi S, Konishi H, Synthesis 2008 1094
242. Nakamura H, Saito H, Nanjo M, Tetrahedron Lett. 2008 49 2697
243. Dell'Acqua M, Abbiati G, Rossi E, Synlett 2010 2672
244. Mori A, Mohamed Ahmed M S., Sekiguki A, Masui K, Koike T, Chem. Lett. 2002 756
245. Ahmed M S. M., Mori A, Org. Lett. 2003 5 3057
246. Ahmed M S. M., Mori A, Tetrahedron 2004 60 9977
247. Gao G.-L, Niu Y.-N, Yan J.-Y, Wang H.-L, Wang G.-W, Shaukat A, Liang Y.-M, J. Org. Chem. 2010 75 1305
248. Li R.-J, Pi S.-F, Liang Y, Wang J.-Q, Song R.-J, Chen G.-X, Li J.-H, Chem. Commun. 2010 46 8183
249. For related spiroacetal epimerization processes, see:, Smith A B. III, Doughty V A., Lin Q, Zhuang L, McBriar M D., Boldi A M., Moser W H., Murase M, Nakayama K, Sobukawa M, Angew. Chem. Int. Ed. 2001 40 191; Angew. Chem. 2001, 113, 197
250. Gaunt M J., Hook D F., Tanner H R., Ley S V., Org. Lett. 2003 5 4815
251. Barluenga J, Mendoza A, Rodríguez F, Fañanás F J., Angew. Chem. 2009 121 1672
252. Pinto A, Neuville L, Zhu Z, Tetrahedron Lett. 2009 50 3602
253. Deng Y, Shi Y, Ma S, Org. Lett. 2009 11 1205
254. Li M, Dixon D J., Org. Lett. 2010 12 3784
255. Beccalli E M., Bernasconi A, Borsini E, Broggini G, Rigamonti M, Zecchi G, J. Org. Chem. 2010 75 6923
256. Kollar L, Modern Carbonylation Methods Wiley-VCH Weinheim 2008
257. Brennfuhrer A, Neumann H, Beller M, ChemCatChem 2009 1 28
258. Kodama S, Nishinaka E, Nomoto A, Sonoda M, Ogawa A, Tetrahedron Lett. 2007 48 6312
259. Szolcsányi P, Gracza T, Spanik I, Tetrahedron Lett. 2008 49 1357
260. Kato K, Mochida T, Takayama H, Kimura M, Moriyama H, Takeshita A, Kanno Y, Inouye Y, Akita H, Tetrahedron Lett. 2009 50 4744
261. Kang S.-K, Kim K.-J, Org. Lett. 2001 3 511
262. Araujo M J., Bom J, Capela R, Casimiro C, Chambel P, Gomes P, Iley J, Lopes F, Morais J, Moreira R, De Oliveira E, Do Rosario V, Vale N, J. Med. Chem. 2005 48 888
263. Vale N, Collins M S., Gut J, Ferraz R, Rosenthal P J., Cushion M T., Moreira R, Gomes P, Bioorg. Med. Chem. Lett. 2008 18 485
264. Ahrendt K A., Borths C J., MacMillan D W. C., J. Am. Chem. Soc. 2000 122 4243
265. Jen W S., Wiener J J. M., MacMillan D W. C., J. Am. Chem. Soc. 2000 122 9874
266. Quellet S J., Tuttle J B., MacMillan D W. C., J. Am. Chem. Soc. 2005 127 32
267. Beccalli E M., Broggini G, Clerici F, Galli S, Kammerer C, Rigamonti M, Sottocornola S, Org. Lett. 2009 11 1563
268. Ninomiya I, Kiguchi T, In The Alkaloids Vol. 38 Brossi A Academic Press San Diego 1990 1
269. The Merck Index 12th ed. Merck and Co. Inc. Whitehouse Station (NY, USA) 1996 231
270. Somei M, Yokoyama Y, Murakami Y, Ninomiya I, Kiguchi T, Naito T, In The Alkaloids Vol. 54 Cordell G A. Academic Press San Diego 2000 191
271. Inuki S, Oishi S, Fujii N, Ohno H, Org. Lett. 2008 10 5239
272. Wakelin L P. G., Waring M J., In Comprehensive Medicinal Chemisty Sammes P G. Pergamon Oxford 1990 703
273. Yue W S., Li J J., Org. Lett. 2002 4 2201
274. Yoon W S., Lee S J., Kang S K., Ha D.-C, Ha J D., Tetrahedron Lett. 2009 50 4492
275. Kumar S, Ila H, Junjappa H, J. Org. Chem. 2009 74 7046
276. Jeffery T, Tetrahedron 1996 52 10113
277. Li J J., J. Org. Chem. 1999 64 8425
278. Heim-Riether A, Gipson K R., Synthesis 2009 1715
279. Watanabe T, Ueda S, Inuki S, Oishi S, Fujii N, Ohno H, Chem. Commun. 2007 4516
280. St. Jean D J. Jr., Poon S F., Schwarzbach J L., Org. Lett. 2007 9 4893
281. Liu C.-Y, Knochel P, J. Org. Chem. 2007 72 7106
282. For a comprehensive reviews, see:, Knölker H.-J, Reddy K R., In The Alkaloids Vol. 65 Cordell G A. Academic Press Amsterdam 2008 1
283. Chianese A R., Rogers S L., Al-Gattas H, Tetrahedron Lett. 2010 51 2241
284. Zheng Y, Yu G, Wu J, Dai W.-M, Synlett 2010 1075
285. Facompré M, Tardy C, Bal-Mahieu C, Colson P, Perez C, Manzanares I, Cuevas C, Bailly C, Cancer Res. 2003 63 7392
286. Marco E, Laine W, Tardy C, Lansiaux A, Iwao M, Ishibashi F, Bailly C, Gago F, J. Med. Chem. 2005 48 3796
287. Ohta T, Fukuda T, Ishibashi F, Iwao M, J. Org. Chem. 2009 74 8143
288. Majumdar K C., Chattopadhyay B, Nath S, Tetrahedron Lett. 2008 49 1609
289. Bernini R, Cacchi S, Fabrizi G, Sferrazza A, Synthesis 2008 729
290. Majumdar K C., Nath S, Chattopadhyay B, Sinha B, Synthesis 2010 3918
291. Murahashi S.-I, Hirano T, Yano T, J. Am. Chem. Soc. 1978 100 348
292. Laine R M., Thomas D W., Cary L W., Buttrill S E., J. Am. Chem. Soc. 1978 100 6527
293. Crawford S S., Knobler C B., Kaesz H D., J. Inorg. Chem. 1977 16 3201
294. Yin C C., Deeming A J., J. Organomet. Chem. 1977 133 123
295. Sepelak D J., Pierpont C G., Barefield E K., Budz J T., Poffenberger C A., J. Am. Chem. Soc. 1976 98 6187
296. Majumdar K C., Mondal S, Chem. Rev. 2011 111 7749
297. Majumdar K C., Mondal S, Ghosh D, Tetrahedron Lett. 2009 50 4781
298. Majumdar K C., Taher A, Debnath P, Synthesis 2009 793
299. Côté J, Collins S K., Synthesis 2009 1499
300. Campeau L.-C, Parisien M, Jean A, Fagnou K, J. Am. Chem. Soc. 2006 128 581
301. Majumdar K C., Chakravorty S, De N, Tetrahedron Lett. 2008 49 3419
302. Wang C, Piel I, Glorius F, J. Am. Chem. Soc. 2009 131 4194
303. Voutchkova A, Coplin A, Leadbeater N E., Crabtree R H., Chem. Commun. 2008 6312
304. Sanchez J D., Avendano C, Menendez J C., Synlett 2008 1371
305. Lafrance M, Fagnou K, J. Am. Chem. Soc. 2006 128 16496
306. Forke R, Krahl M P., Däbritz F, Jäger A, Knolker H.-J, Synlett 2008 1870
307. Bi W, Yun X, Fan Y, Qi X, Du Y, Huang J, Synlett 2010 2899
308. Weng B, Liu R, Li J.-H, Synthesis 2010 2926
309. Ackermann L, Althammer A, Mayer P, Synthesis 2009 3493
310. Ackermann L, Vicente R, Born R, Adv. Synth. Catal. 2008 350 741
311. Ackermann L, Jeyachandran R, Potukuchi H K., Novak P, Buttner L, Org. Lett. 2010 12 2056
312. Jiang H, Feng Z, Wang A, Liu X, Chen Z, Eur. J. Org. Chem. 2010 1227
313. Colquhoun H M., Thompson D J., Twigg M V., Carbonylation: Direct Synthesis of Carbonyl Compounds Plenum Press New York/London 1991
314. Beller M, Cornils B, Frohning C D., Kohlpaintner C W., J. Mol. Catal. A 1995 104 17
315. Skoda-Foldes R, Kollar L, Curr. Org. Chem. 2002 6 1097
316. Worlikar S A., Larock R C., J. Org. Chem. 2008 73 7175
317. Minatti A, Muniz K, Chem. Soc. Rev. 2007 36 1142
318. Mori M, Chiba K, Ohta N, Ban Y, Heterocycles 1979 13 329
319. Perry R J., Turner S R., J. Org. Chem. 1991 56 6573
320. Cho C S., Ren W S., Tetrahedron Lett. 2009 50 2097
321. Yao T, Yue D, Larock R C., J. Org. Chem. 2005 70 9985
322. Papers related to the biological activity:, Engelmeier D, Hadacek F, Hofer Q, Lutz-Kutschera G, Nagl M, Wurz G, Greger H, J. Nat. Prod. 2004 67 19
323. Bouberte M Y., Krohn K, Hussain H, Dongo E, Schulz B, Hu W, Nat. Prod. Res. 2006 20 842
324. On palladium-catalyzed isocoumarin synthesis:, Konno F, Ishikawa M, Kawahata M, Yamaguchi K, J. Org. Chem. 2006 71 9818
325. For a review of isocoumarin syntheses, see:, Napolitano E, Org. Prep. Proced. Int. 1997 29 631
326. For the preparation of enol lactones using a carbonylation protocol, see:, Uozumi Y, Mori E, Mori M, Shibasaki M, J. Organomet. Chem. 1990 399 93
327. Negishi E.-i, Copéret C, Sugihara T, Shimoyama I, Zhang Y, Wu G, Tour J M., Tetrahedron 1994 50 425
328. Tadd A C., Fielding M R., Willis M C., Chem. Commun. 2009 6744
329. Uchiyama M, Ozawa H, Takuma K, Matsumoto Y, Yonehara M, Hiroya K, Sakamoto T, Org. Lett. 2006 8 5517
330. Zhang H, Matsuda H, Kumahara A, Ito Y, Nakamura S, Yoshikawa M, Bioorg. Med. Chem. Lett. 2007 17 4972
331. Kurume A, Kamata Y, Yamashita M, Wang Q, Matsuda H, Yoshikawa M, Kawasaki I, Ohta S, Chem. Pharm. Bull. 2008 56 1264
332. Alper H, Zheng Z, Org. Lett. 2008 10 829
333. Zheng Z, Alper H, Org. Lett. 2008 10 4903
334. Zeng F, Alper H, Org. Lett. 2010 12 3642
335. Rescourio G, Alper H, J. Org. Chem. 2008 73 1612
336. Orain D, Blumstein A.-C, Tasdelen E, Haessig S, Synlett 2008 2433
337. Tsuritani T, Yamamoto Y, Kawasaki M, Mase T, Org. Lett. 2009 11 1043
338. Venkatesh C, Sundaram G S. M., Ha H, Junjappa H, J. Org. Chem. 2006 71 1280
339. Tokunaga T, Hume W E., Umezome T, Okazaki K, Ueki Y, Kumagai K, Hourai S, Nagamine J, Seki H, Taiji M, Noguchi H, Nagata R, J. Med. Chem. 2001 44 46411
340. Hewawasam P, Erway M, Moon S L., Knipe J, Weiner H, Boissard C G., Post-Munson D J., Gao Q, Huang S, Gribkoff V K., Meanwell N A., J. Med. Chem. 2002 45 1487
341. Lee S, Hartwig J F., J. Org. Chem. 2001 66 3402
342. Hillgren J M., Marsden S P., J. Org. Chem. 2008 73 6459
343. Salcedo A, Neuville L, Zhu J, J. Org. Chem. 2008 73 3600
344. Liu G, Lu X, Tetrahedron 2008 64 7324
345. Felpin F.-X, Ibarguren O, Nassar-Hardy L, Fouquet E, J. Org. Chem. 2009 74 1349
346. Ibarguren O, Zakri C, Fouquet E, Felpin F.-X, Tetrahedron Lett. 2009 50 5071
347. Leclerc J.-P, André M, Fagnou K, J. Org. Chem. 2006 71 1711
348. Hitce J, Baudoin O, Adv. Synth. Catal. 2007 349 2054
349. Felpin F.-X, Fouquet E, Adv. Synth. Catal. 2008 350 863
350. Kantam L K., Chakravarti R, Chintareddy V R., Sreedhar B, Bhargava S, Adv. Synth. Catal. 2008 350 2544
351. Audia J E., Evrard D A., Murdoch G R., Droste J J., Nissen J S., Schenck K W., Fludzinski P, Lucaites V L., Nelson D L., Cohen M L., J. Med. Chem. 1996 39 2773
352. Peat A J., Buchwald S L., J. Am. Chem. Soc. 1996 118 1028
353. King H D., Meng Z, Denhart D, Mattson R, Kimura R, Wu D, Gao Q, Macor J E., Org. Lett. 2005 7 3437
354. Higuchi K, Kawasaki T, Nat. Prod. Rep. 2007 24 843
355. Xu Z, Hu W, Zhang F, Li Q, Lu Z, Zhang L, Jia Y, Synthesis 2008 3981
356. Hu C, Qin H, Cui Y, Jia Y, Tetrahedron 2009 65 9075
357. Kuriyama M, Ishiyama N, Shimazawa R, Shirai R, Onomura O, J. Org. Chem. 2009 74 9210
358. Wang S, Xie K, Tan Z, An X, Zhaou X, Guo C.-C, Peng Z, Chem. Commun. 2009 6469
359. Bowman W R., Lyon J E., Pritchard G J., Synlett 2008 2169