Palladium-catalyzed alkynylation of aryl and hetaryl halides: A journey from conventional palladium complexes or salts to palladium/carbon

Synlett

Volumn , Issue 18, 2009, Pages 2896-2912

  Pal, Manojit ^a  

^a Matrix Laboratories Limited   (India)

Author keywords

Alkynylation; Aryl halides; Catalysis; Palladium; Palladium carbon; Sonogashira reaction

Indexed keywords

CARBON; HALIDE; PALLADIUM; PALLADIUM COMPLEX; SODIUM CHLORIDE;

ALKYNYLATION; CATALYSIS; CATALYST; CHEMISTRY; OUTCOME ASSESSMENT; REVIEW; SONOGASHIRA REACTION;

EID: 72049112575     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218021     Document Type: Review

References (137)

1. Present address: Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500046, Andhra Pradesh, India; Fax +914066571581.
2. Sonogashira K, Tohda Y, Hagihara N, Tetrahedron Lett. 1975 4467
3. Sonogashira K, Yatake T, Tohda Y, Takahashi S, Hagihara N, J. Chem. Soc., Chem. Commun. 1977 291
4. Takahashi S, Kuroyama Y, Sonogashira K, Hagihara N, Synthesis 1980 627
5. Dasgupta S K., Pal M, Mahanty J S., Kundu N G., Novel5-Substituted Uracil Derivatives as Inhibitors of Thymidylate Synthesis Enzyme Paper number CP22 15th National Symposium on Organic Chemistry (NASOC-XV) Calcutta March 22-23, 1994
6. Kundu N G., Das B, Spears C P., Majumdar A, Kang S I., J. Med. Chem. 1990 33 1975
7. Kundu N G., Dasgupta S K., J. Chem. Soc., Perkin Trans. 1 1993 2657
8. Kundu N G., Pal M, Chowdhury C, J. Chem. Res., Synop. 1995 4
9. Stephens R D., Castro C E., J. Org. Chem. 1963 28 3313
10. Robins M J., Barr P J., J. Org. Chem. 1983 48 1854
11. Kundu N G., Pal M, Mahanty J S., Dasgupta S K., J.Chem.Soc., Chem. Commun. 1992 41
12. Kundu N G., Pal M, Mahanty J S., De M, J. Chem. Soc., Perkin Trans. 1 1997 2815
13. Kundu N G., Pal M, J. Chem. Soc., Chem. Commun. 1993 86
14. Kundu N G., Pal M, Nandi B, J. Chem. Soc., Perkin Trans. 1 1998 561
15. Arcadi A, Cacchi S, Marinelli F, Synthesis 1986 749
16. Kundu N G., Pal M, Chowdhury C, J. Chem. Res. 1993 432
17. Rossi R, Carpita A, Bigelli C, Tetrahedron Lett. 1985 26 523
18. Pal M, Kundu N G., J. Chem. Soc., Perkin Trans. 1 1996 449
19. Alonso F, Beletskaya I P., Yus M, Chem. Rev. 2004 104 3079
20. Krisch G, Hesse S, Comel A, Curr. Org. Synth. 2004 1 47
21. Zeni G, Larock R C., Chem. Rev. 2006 106 4644
22. Patil N T., Yamamoto Y, Chem. Rev. 2008 108 3395
23. Chinchilla R, Nájera C, Chem. Rev. 2007 107 874
24. DelaRosa M A., Velarde E, Guzman A, Synth. Commun. 1990 20 2059
25. Novak Z, Szabo A, Repasi J, Kotschy A, J. Org. Chem. 2003 68 3327
26. 2/C as catalyst, see:, Mori Y, Seki M, J. Org. Chem. 2003 68 1571
27. Heidenreich R G., Köhler K, Krauter J G. E., Pietsch J, Synlett 2002 1118
28. Felpin F.-X, Vo-Thanh G, Villiéras J, Lebreton J, Tetrahedron: Asymmetry 2001 12 1121
29. Bates R W., Boonsombat J, J. Chem. Soc., Perkin Trans. 1 2001 654
30. Bleicher L S., Cosford N D. P., Herbaut A, McCallum J S., McDonald I A., J. Org. Chem. 1998 63 1109
31. Bleicher L, Cosford N D. P., Synlett 1995 1115
32. Potts K T., Horwitz C P., Fessak A, Keshavarz K M., Nash K E., Toscano P J., J. Am. Chem. Soc. 1993 115 10444
33. Yin L X., Liebscher J, Chem. Rev. 2007 107 133
34. Seki M, Synthesis 2006 2975
35. Pal M, Parasuraman K, Gupta S, Yeleswarapu K R., Synlett 2002 1976
36. For a review, see:, Pal M, Tetrahedron 2009 65 433
37. Rao Y K., Pal M, Sharma V M., Venkateswarlu A, Pillaresetti R, Patent Application US 2005/0119269 A1 June 2, 2005
38. Pal M, Subramanian V, Parasuraman K, Yeleswarapu K R., Tetrahedron 2003 59 9563
39. Kalai T, Kulcsar G, Osz E, Jeko J, Sumegi B, Hideg K, Arkivoc 2004 (vii) 266
40. Pal M, Dakarapu R, Parasuraman K, Subramanian V, Yeleswarapu K R., J. Org. Chem. 2005 70 7179
41. Pal M, Parasuraman K, Subramanian V, Dakarapu R, Yeleswarapu K R., Tetrahedron Lett. 2004 45 2305
42. Li C.-J, Chem. Rev. 2005 105 3095
43. Bhattacharya S, Sengupta S, Tetrahedron Lett. 2004 45 8733
44. Cacchi S, Fabrizi G, Goggiamani A, Curr. Org. Chem. 2006 10 1423
45. Dai W.-M, Lai K W., Tetrahedron Lett. 2002 43 9377
46. Pal M, Subramanian V, Yeleswarapu K R., Tetrahedron Lett. 2003 44 8221
47. Xu G, Searle L L., Hughes T V., Beck A K., Connolly P J., Abad M C., Neeper M P., Struble G T., Springer B A., Emanuel [nl]S L., Gruninger R H., Pandey N, Adams M, Moreno-Mazza S, Fuentes-Pesquera A R., Middleton S A., Greenberger L M., Bioorg. Med. Chem. Lett. 2008 18 3495
48. Heidenreich R.-G, Krauter J G. E., Pietsch J, Köheler K, J. Mol. Catal. A: Chem. 2002 182-183 499
49. Tagata T, Nishida M, J. Org. Chem. 2003 68 9412
50. Pal M, Batchu V R., Subramanian V, Parasuraman K, Swamy N K., Kumar S, Tetrahedron 2005 61 9869
51. Subramanian V, Batchu V R., Pal M, An Improved Synthesis of 2-Substituted Benzo[b]furans in Water under Pd/C-Cu Catalysis Paper number P15 Indo-US Conference on Recent Advances in Organometallic Catalysis and Olefin Polymerization IIT Madras/Chennai/India December 10-12, 2003
52. Bong D T., Ghadiri M R., Org. Lett. 2001 3 2509
53. Raju S, Kumar P R., Mukkanti K, Annamalai P, Pal M, Bioorg. Med. Chem. Lett. 2006 6185
54. Reddy E A., Barange D K., Islam A, Mukkanti K, Pal M, Tetrahedron 2008 64 7143
55. Reddy E A., Islam A, Mukkanti K, Bandameedi V, Bhownik D R., Pal M, Beilstein J. Org. Chem. 2009 5 No32 (DOI: 10.3762/bjoc.5.32)
56. Nolan J M., Comins D L., J. Org. Chem. 2003 68 3736
57. Elangoven A, Chen T.-Y, Chen C.-Y, Ho T.-I, Chem. Commun. 2003 2146
58. Seck M, Franck X, Hocquemiller R, Figadère B, Peyrat J.-F, Provot O, Brion J.-D, Alami M, Tetrahedron Lett. 2004 45 1881
59. Rodriguez J G., delosRios C, Lafuente A, Tetrahedron 2005 61 9042
60. Toyota M, Komori C, Ihara M, J. Org. Chem. 2000 65 7110
61. Ciufolini M A., Mitchell J W., Roschangar F, Tetrahedron Lett. 1996 37 8281
62. Yamanaka H, Shiraiwa M, Edo K, Sakamoto T, Chem. Pharm. Bull. 1979 27 270
63. Belmont P, Andrez J.-C, Allan C S. M., Tetrahedron Lett. 2004 45 2783
64. Cacchi S, Fabrizi G, Chem. Rev. 2005 105 2873
65. Patil S, Buolamwini J K., Curr. Org. Synth. 2006 3 477
66. Pal M, Subramanian V, Batchu V R., Dager I, Synlett 2004 1965
67. Sakamoto T, Kondo Y, Iwashita S, Nagano T, Yamanaka H, Chem. Pharm. Bull. 1988 36 1305
68. Amjad M, Knight D W., Tetrahedron Lett. 2004 45 539
69. Mackman R L., Katz B A., Breitenbucher J G., Hui H C., Verner E, Luong C, Liu L, Sprengeler P A., J. Med. Chem. 2001 44 3856
70. Kundu N G., Mahanty J S., Das P, Das B, Tetrahedron Lett. 1993 34 1625
71. Takeda A, Kamijo S, Yamamoto Y, J. Am. Chem. Soc. 2000 122 5662
72. Liao H.-Y, Cheng C.-H, J. Org. Chem. 1995 60 3711
73. Kanazawa C, Terada M, Tetrahedron Lett. 2007 48 933
74. Uchiyama M, Ozawa H, Takuma K, Matsumoto Y, Yonehara M, Hiroya K, Sakamoto T, Org. Lett. 2006 8 5517
75. Barange D K., Batchu V R., Pal M, First Pd/C-Mediated Synthesis of (Z)-3-Alkynylidene Phthalides Joint International Conference on Building Bridges Forging Bonds (ACS-CSIR OCCB) Pune / India January 7-9, 2006
76. Zhou L, Jiang H.-F, Tetrahedron Lett. 2007 48 8449
77. Raju S, Batchu V R., Swamy N K., Dev R V., Babu J M., Kumar P R., Mukkanti K, Pal M, Tetrahedron Lett. 2006 47 83
78. Raju S, Batchu V R., Swamy N K., Dev R V., Sreekanth B R., Babu J M., Vyas K, Kumar P R., Mukkanti K, Annamalai P, Pal M, Tetrahedron 2006 62 9554
79. Queiroz M.-J R. P., Calhelha R C., Vale-Silva L A., Pinto E, Nascimento M S.-J, Eur. J. Med. Chem. 2009 44 1893
80. Pal M, Kalleda S, Padakanti S, Kumara Swamy N, Yeleswarapu K R., Alexander C W., Khanna I, Iqbal J, Pillarisetti S, Barange D, Patent Application US 2006/0084645 A1 April 20, 2006
81. Pal M, Batchu V R., Swamy N K., Padakanti S, Tetrahedron Lett. 2006 47 3923
82. McGuigan C, Barucki H, Blewett S, Carangio A, Erichsen J T., Andrei G, Snoeck R, De Clercq E, Balzarini J, J. Med. Chem. 2000 43 4993
83. McGuigan C, Brancale A, Andrei G, Snoeck R, De Clercq E, Balzarini J, Bioorg. Med. Chem. Lett. 2000 10 1215
84. McGuigan C, Yarnold C J., Jones G, Velazquez S, Barucki H, Brancale A, Andrei G, Snoeck R, De Clercq E, Balzarini J, J. Med. Chem. 1999 42 4479
85. Janeba Z, Balzarini J, Andrei G, Snoeck R, De Clercq E, Robins M J., J. Med. Chem. 2005 48 4690
86. Venkataraman S, Barange D K., Pal M, Tetrahedron Lett. 2006 47 7317
87. Layek M, Gajare V, Kalita D, Islam A, Mukanti K, Pal M, Tetrahedron Lett. 2009 50 3867
88. See also, Layek M, Rao A. V D., Gajare V, Kalita D, Barenge D K., Islam A, Mukkanti K, Pal M, Tetrahedron Lett. 2009 50 4878
89. Harmata M, Rayanil K.-o, Gomes M G., Zheng P, Calkins N L., Kim S.-Y, Fan Y, Bumbu V, Lee D R., Wacharasindhu S, Hong X, Org. Lett. 2005 7 143
90. For benzo[b]furans, see:, Banwell M G., Flynn B L., Willis A C., Hamel E, Aust. J. Chem. 1999 52 767
91. Arcadi A, Cacchi S, Fabrizi G, Marinelli F, Moro L, Synlett 1999 1432
92. Colobert F, Castanet A.-S, Abillard O, Eur. J. Org. Chem. 2005 3334
93. Yue D, Yao T, Larock R C., J. Org. Chem. 2005 70 10292
94. For benzo[b]thiophenes, see:, Yue D, Larock R C., J. Org. Chem. 2002 67 1905
95. Hessian K O., Flynn B L., Org. Lett. 2003 5 4377
96. For furopyridines, see:, Arcadi A, Cacchi S, Di Giuseppe S, Fabrizi G, Marinelli F, Org. Lett. 2002 4 2409
97. For furoquinolines, see:, Aillaud I, Bossharth E, Conreaux D, Desbordes P, Monteiro N, Balme G, Org. Lett. 2006 8 1113
98. For furopyrimidines, see:, Rao M S., Esho N, Sergeant C, Roman D, J. Org. Chem. 2003 68 6788
99. For indoles, see:, Yue D, Larock R C., Org. Lett. 2004 6 1037
100. Barluenga J, Trincado M, Rubio E, Gonzalez J M., Angew. Chem. Int. Ed. 2003 42 2406
101. Yao D, Yue D, Larock R C., J. Comb. Chem. 2005 7 809
102. For isoquinolines and naphthyridines, see:, Huang Q, Hunter J A., Larock R C., J. Org. Chem. 2002 67 3437
103. For isoindolinones, see:, Yao T, Larock R C., J. Org. Chem. 2005 70 1432
104. For isochromenes, see:, Barluenga J, Vazquez-Villa H, Ballesteros A, Gonzalez J M., J. Am. Chem. Soc. 2003 125 9028
105. Yue D, DellaCa N, Larock R C., Org. Lett. 2004 6 1581
106. For isocoumarins, see:, Yao T, Larock R C., J. Org. Chem. 2003 68 5936
107. Rossi R, Carpita A, Bellina F, Stabile P, Mannina L, Tetrahedron 2003 59 2067
108. For phosphaisocoumarins, see:, Peng A.-Y, Ding Y.-X, Org. Lett. 2004 6 1119
109. For coumestans, see:, Yao T, Yue D, Larock R C., J. Org. Chem. 2005 70 9985
110. For other examples of iodonium-promoted heterocyclizations of acetylenic compounds, see:, Sniady A, Wheeler K A., Dembinski R, Org. Lett. 2005 7 1769
111. Liu Y, Song F, Cong L, J. Org. Chem. 2005 70 6999
112. Yao T, Zhang X, Larock R C., J. Org. Chem. 2005 70 7679
113. Liu Y, Zhou S, Org. Lett. 2005 7 4609
114. Waldo J P., Larock R C., Org. Lett. 2005 7 5203
115. For iodocyclization of sulfonamide derivatives of [nl] o -(alk-1-ynyl)anilines leading to 3-iodoindoles, see:, Amjad M, Knight D W., Tetrahedron Lett. 2004 45 539
116. Barange D K., Batchu V R., Gorja D, Pattabiraman V R., Tatini L K., Babu J M., Pal M, Tetrahedron 2007 63 1775
117. Barange D K., Nishad T C., Swamy N K., Bandameedi V, Kumar D, Sreekanth B R., Vyas K, Pal M, J. Org. Chem. 2007 72 8547
118. Hesse S, Kirsch G, Synthesis 2001 755
119. Hesse S, Kirsch G, Tetrahedron Lett. 2002 43 1213
120. Hesse S, Kirsch G, Synthesis 2003 717
121. Bera R, Swamy N K., Dhananjaya G, Babu J M., Kumar P R., Mukkanti K, Pal M, Tetrahedron 2007 63 13018
122. Snieckus V, Chem. Rev. 1990 90 879
123. Lautens M, Klute W, Tam W, Chem. Rev. 1996 96 49
124. Saito S, Yamamoto Y, Chem. Rev. 2000 100 2901
125. Yamamoto Y, Ishii J.-I, Nishiyama H, Itoh K, J. Am. Chem. Soc. 2004 126 3712
126. Saito S, Chounan Y, Nogami T, Fukushi T, Tsuboya N, Yamada Y, Kitahara H, Yamamoto Y, J.Org.Chem. 2000 65 5350
127. Gevorgyan V, Tsuboya N, Yamamoto Y, J. Org. Chem. 2001 66 2743
128. Saito S, Salter M M., Gevorgyan V, Tsuboya N, Tando K, Yamamoto Y, J. Am. Chem. Soc. 1996 118 3970
129. references cited therein, Gevorgyan V, Takeda A, Homma M, Sadayori N, Radhakrishnan U, Yamamoto Y, J. Am. Chem. Soc. 1999 121 6391
130. For a sequential one-pot procedure involving Sonogashira coupling and homo-benzannulation for the synthesis of [nl]6 H -dibenzo[ b,d ]pyran-6-ones, see:, Kawasaki T, Yamamoto Y, J. Org. Chem. 2002 67 5138
131. Xi C, Chen C, Lin J, Hong X, Org. Lett. 2005 7 347
132. Swamy N K., Tatini L K., Babu J M., Annamalai P, Pal M, Chem. Commun. 2007 1035
133. Batchu V R., Barange D K., Kumar D, Sreekanth B R., Vyas K, Reddy E A., Pal M, Chem. Commun. 2007 1966
134. Rostovtsev V V., Green L G., Fokin V V., Sharpless K B., Angew. Chem. Int. Ed. 2002 41 2596
135. Tornøe C W., Christensen C, Meldal M, J. Org. Chem. 2002 67 3057
136. Kamijo S, Jin T, Huo Z, Yamamoto Y, J. Am. Chem. Soc. 2003 125 7786
137. Chowdhury C, Mandal S B., Achari B, Tetrahedron Lett. 2005 46 8531