Transition-metal-catalyzed cross-couplings going green: In water at room temperature

Aldrichimica Acta

Volumn 41, Issue 3, 2008, Pages 59-72

  Lipshutz, Bruce H ^a   Ghorai, Subir ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Cross couplings; Designer surfactants; Green chemistry; Micellar catalysis; PTS

Indexed keywords

EID: 56549128663     PISSN: 00025100     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (132)

1. Sheldon, R. A. Green Chem. 2007, 9, 1273.
2. Trost, B. M. Science 1991, 254, 1471.
3. (a) Li, C.-J.; Chan, T.-H. Comprehensive Organic Reactions in Aqueous Media, 2nd ed.; Wiley-VCH: Hoboken, NJ, 2007.
4. (b) Sheldon, R. A.; Arends, I.; Hanefeld, U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim, Germany, 2007.
5. (c) Organic Reactions in Water: Principles, Strategies, and Applications; Lindström, U. M., Ed.; Blackwell Publishing: Oxford, U.K., 2007.
6. (d) 12th Annual Green Chemistry and Engineering Conference; ACS Green Chemistry Institute, Washington, D.C., June 24-26, 2008 (http://www.gcande.org/; accessed July 24, 2008).
7. (a) Sheldon, R. A. Green Chem. 2005, 7, 267.
8. (b) Green Chem. 2003, 5, 99. (Special Issue on Green Solvents for Catalysis; Leitner, W., Seddon, K. R., Wasserscheid, P., Eds.)
9. Blackmond, D. G.; Armstrong, A.; Coombe, V.; Wells, A. Angew. Chem., Int. Ed. 2007, 46, 3798.
10. (a) Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275.
11. (b) Hayashi, Y. Angew. Chem., Int. Ed. 2006, 45, 8103.
12. (c) Breslow, R. Acc. Chem. Res. 1991, 24, 159.
13. (d) Pihko, P. M.; Laurikainen, K. M.; Usano, A.; Nyberg, A. I.; Kaavi, J. A. Tetrahedron 2006, 62, 317.
14. (e) Nyberg, A. I.; Usano, A.; Pihko, P. M. Synlett 2004, 1891.
15. (a) Dwars, T.; Paetzold, E.; Oehme, G. Angew. Chem., Int. Ed. 2005, 44, 7174.
16. (b) Khan, M. N. Micellar Catalysis; CRC Press: Boca Raton, FL, 2006.
17. Huibers, P. D. T.; Lobanov, V. S.; Katritzky, A. R.; Shah, D. O.; Karelson, M. Langmuir 1996, 12, 1462.
18. (a) Dynamics of Surfactant Self-Assemblies: Micelles, Microemulsions, Vesicles, and Lyotropic Phases; Zana, R., Ed.; Surfactant Science Series 125; Taylor & Francis: Boca Raton, FL, 2005.
19. (b) Myers, D. Surfactant Science and Technology, 3rd ed.; Wiley: Hoboken, NJ, 2006.
20. (a) Ogawa, C.; Kobayashi, S. Acid Catalysis in Water. In Organic Reactions in Water: Principles, Strategies, and Applications; Lindström, U. M., Ed.; Blackwell Publishing: Oxford, U.K., 2007; Chapter 3, pp 60-91.
21. (b) Li, C.-J. Metal-Mediated C-C Bond Formations in Aqueous Media. In Organic Reactions in Water: Principles, Strategies, and Applications; Lindström, U. M., Ed.; Blackwell Publishing: Oxford, U.K., 2007;
22. Chapter 4. (c) Li, C.-J.; Chen, L. Chem. Soc. Rev. 2006, 35, 68.
23. (a) Organometallics in Synthesis: A Manual, 2nd ed.; Schlosser, M., Ed.; Wiley: Chichester, U.K., 2002.
24. (b) Beletskaya, I. P.; Cheprakov, A. V. Aqueous Palladium Catalysis. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, NY, 2002; Vol. 2, Part X.1, pp 2957-3006.
25. (a) Kobayashi, S.; Wakabayashi, T.; Nagayama, S.; Oyamada, H. Tetrahedron Lett. 1997, 38, 4559.
26. (b) Kobayashi, S.; Wakabayashi, T.; Oyamada, H. Chem. Lett. 1997, 831.
27. (c) Kobayashi, S.; Busujima, T.; Nagayama, S. Synlett 1999, 545.
28. (d) Kobayashi, S.; Busujima, T.; Nagayama, S. J. Chem. Soc., Chem. Commun. 1998, 19.
29. Borkovec, M. Measuring Particle Size by Light Scattering. In Handbook of Applied Surface and Colloid Chemistry; Holmberg, K., Ed.; Wiley: Chichester, U.K., 2002; Vol. 2, pp 357-370.
30. Wei, H.; Cheng, C.; Chang, C.; Chen, W.-Q.; Cheng, S.-X.; Zhang, X.-Z.; Zhuo, R.-X. Langmuir 2008, 24, 4564.
31. (a) Kürti, L.; Czakó, B. Strategic Applications of Named Reactions in Organic Synthesis: Background and Detailed Mechanisms; Elsevier Academic Press: Burlington, MA, 2005.
32. (b) Li, J. J. Name Reactions, 2nd ed.; Springer-Verlag: New Delhi, India, 2003.
33. (a) Borowy-Borowski, H.; Sikorska-Walker, M.; Walker, P. R. Water-Soluble Compositions of Bioactive Lipophilic Compounds. U.S. Patent 6,045,826, Apr 4, 2000.
34. (b) Borowy-Borowski, H.; Sikorska-Walker, M.; Walker, P. R. Water-Soluble Compositions of Bioactive Lipophilic Compounds. U.S. Patent 6,191,172, Feb 20, 2001.
35. (c) Borowy-Borowski, H.; Sikorska-Walker, M.; Walker, P. R. Water-Soluble Compositions of Bioactive Lipophilic Compounds. U.S. Patent 6,632,443, Oct 14, 2003.
36. For a summary of the properties of TRITON® X-100 (CAS Registry No. 9002-93-1), see http://www.sigmaaldrich.com/sigma/product%20information%20sheet/ t8532pis.pdf (accessed Jul 2008).
37. For more information on BRIJ® 30 (CAS Registry No. 9002-92-0), see Satkowski, W. B.; Huang, S. K.; Liss, R. L. Polyoxyethylene Alcohols. In Nonionic Surfactants; Schick, M. J., Ed.; Dekker: New York, 1967; pp 86-141.
38. For more information on TWEEN® 80 (CAS Registry No. 9005-65-6), see http://en.wikipedia.org/wiki/Polysorbate_80#cite_note-DannyK-3 (accessed Jul 2008).
39. For a discussion of the properties of sodium dodecyl sulfate (CAS Registry No. 151-21-3), see Powney, J.; Addison, C. C. The Properties of Detergent Solutions. Trans. Faraday Soc. 1937, 33, 1243.
40. For applications and properties of Eastman Vitamin E TPGS NF, see http://www.eastman.com/NR/rdonlyres/A2FE037B-0778-4A90-A0FC-5D07BE51064A/0/ PCI102.pdf (accessed Jul 2008).
41. (a) Griffin, W. C. J. Soc. Sosmet. Chem. 1949, 1, 311.
42. (b) Niraula, B. B.; Chun, T. K.; Othman, H.; Misran, M. Colloids Surf., A: Physicochem. Eng. Aspects 2004, 248, 157.
43. (a) Lumb, K. J.; DeCarr, L. B.; Milardo, L. F.; Mays, M. R.; Buckholz, T. M.; Fisk, S. E.; Pellegrino, C. M.; Ortiz, A. A.; Mahle, C. D. J. Med. Chem. 2007, 50, 2264.
44. (b) Gatouillat, G.; Odot, J.; Balasse, E.; Nicolau, C.; Tosi, P.-F.; Hickman, D. T.; López-Deber, M. P.; Madoulet, C. Cancer Lett. 2007, 257, 165.
45. (c) Li, J.; Kao, W. J. Biomacromolecules 2003, 4, 1055.
46. Naderi, J.; Somayajulu-Nitu, M.; Mukerji, A.; Sharda, P.; Sikorska, M.; Borowy-Borowski, H.; Antonsson, B.; Pandey, S. Apoptosis 2006, 11, 1359.
47. Lipshutz, B. H.; Taft, B. R. Org. Lett. 2008, 10, 1329.
48. (a) González, Y. I.; Kaler, E. W. Curr. Opin. Colloid Interf. Sci. 2005, 10, 256.
49. (b) Cryo-TEM data was provided by Dr. Jingshan Dong at the NSF Regional Center, University of Minnesota.
50. Borowy-Borowski, H.; Berl, V.; Lipshutz, B. H. University of California, Santa Barbara, CA. Unpublished work.
51. (a) Lipshutz, B. H.; Taft, B. R. University of California, Santa Barbara, CA.
52. Unpublished work, (b) Huang, Z.-Z.; Ye, S.; Xia, W.; Yu, Y.-H.; Tang, Y. J. Org. Chem. 2002, 67, 3096.
53. (a) Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972, 37, 2320.
54. See also: (b) Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, U.K., 2000.
55. (c) Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century; Wiley: Chichester, U.K., 2004.
56. (a) Knowles, J. P.; Whiting, A. Org. Biomol. Chem. 2007, 5, 31.
57. (b) Phan, N. T. S.; van der Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609.
58. (c) See reference 11b.
59. (d) Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677.
60. (e) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
61. (a) Alacid, E.; Najera, C. Synlett 2006, 2959.
62. (b) Schönfelder, D.; Nuyken, O.; Weberskirch, R. J. Organomet. Chem. 2005, 690, 4648.
63. (c) Schönfelder, D.; Fischer, K.; Schmidt, M.; Nuyken, O.; Weberskirch, R. Macromolecules 2005, 38, 254.
64. Jeffery, T. Tetrahedron Lett. 1994, 35, 3051.
65. Bumagin, N. A.; Bykov, V. V.; Sukhomlinova, L. I.; Tolstaya, T. P.; Beletskaya, I. P. J. Organomet. Chem. 1995, 486, 259.
66. Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170.
67. Bhattacharya, S.; Srivastava, A.; Sengupta, S. Tetrahedron Lett. 2005, 46, 3557.
68. Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2005, 61, 11771.
69. (a) Menger, F. M.; Portnoy, C. E. J. Am. Chem. Soc. 1967, 89, 4698.
70. (b) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409.
71. 2] (CAS Registry No. 95408-45-0) was kindly supplied to us by Dr. Thomas J. Colacot, Johnson Matthey (email: colactj@jmusa.com).
72. (b) Lipshutz, B. H.; Taft, B. R.; Ghorai, S. University of California, Santa Barbara, CA. Unpublished work.
73. Lipshutz, B. H.; Monzon, G. A.; Abela, A. R.; Taft, B. R. University of California, Santa Barbara, CA. Unpublished work.
74. Lipshutz, B. H.; Petersen, T. B.; Abela, A. R. Org. Lett. 2008, 10, 1333.
75. Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2008, 64, 3047.
76. DeVasher, R. B.; Moore, L. R.; Shaughnessy, K. H. J. Org. Chem. 2004, 69, 7919.
77. Huang, R.; Shaughnessy, K. H. Organometallics 2006, 25, 4105.
78. Ramesh Kumar, N. S. C.; Victor Paul Raj, I.; Sudalai, A. J. Mol. Cat., A: Chem. 2007, 269, 218.
79. (a) Lee, M.; Jang, C.-J.; Ryu, J.-H. J. Am. Chem. Soc. 2004, 126, 8082.
80. (b) Ryu, J.-H.; Jang, C.-J.; Yoo, Y.-S.; Lim, S.-G.; Lee, M. J. Org. Chem. 2005, 70, 8956.
81. Basheer, C.; Hussain, F. S. J.; Lee, H. K.; Valiyaveettil, S. Tetrahedron Lett. 2004, 45, 7297.
82. Anderson, K. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2005, 44, 6173.
83. Bedford, R. B.; Blake, M. E.; Butts, C. P.; Holder, D. Chem. Commun. 2003, 466.
84. Arcadi, A.; Cerichelli, G.; Chiarini, M.; Correa, M.; Zorzan, D. Eur. J. Org. Chem. 2003, 4080.
85. Zhang, W.; Chen, C. H.-T.; Lu, Y.; Nagashima, T. Org. Lett. 2004, 6, 1473.
86. Lipshutz, B. H.; Abela, A. R. Org. Lett., submitted for publication.
87. (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
88. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
89. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
90. (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592.
91. (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
92. (f) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003 (three-volume set).
93. (g) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199.
94. (h) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490.
95. (i) Gradillas, A.; Pérez-Castells, J. Angew. Chem., Int. Ed. 2006, 45, 6086.
96. (j) Schrodi, Y.; Pederson, R. L. Aldrichimica Acta 2007, 40, 45.
97. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
98. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
99. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
100. Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J., Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791.
101. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168.
102. Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 2403.
103. Grela, K.; Harutyunyan, S.; Michrowska, A. Angew. Chem., Int. Ed. 2002, 41, 4038.
104. Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674.
105. (a) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317.
106. (b) Kirkland, T. A.; Lynn, D. M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 9904.
107. (c) Lynn, D. M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 3187.
108. Gallivan, J. P.; Jordan, J. P.; Grubbs, R. H. Tetrahedron Lett. 2005, 46, 2577.
109. Samanta, D.; Kratz, K.; Zhang, X.; Emrick, T. Macromolecules 2008, 41, 530.
110. Jordan, J. P.; Grubbs, R. H. Angew. Chem., Int. Ed. 2007, 46, 5152.
111. Hong, S. H.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 3508.
112. Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002, 12, 1873.
113. Connon, S. J.; Rivard, M.; Zaja, M.; Blechert, S. Adv. Synth. Catal. 2003, 345, 572.
114. Rix, D.; Caïjo, F.; Laurent, I.; Gułajski, Ł.; Grela, K.; Mauduit, M. Chem. Commun. 2007, 3771.
115. For a review on aqueous olefin metathesis, see Burtscher, D.; Grela, K. Angew. Chem., Int. Ed. 2008, 47, in press.
116. Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
117. Lipshutz, B. H.; Aguinaldo, G. T.; Ghorai, S.; Voigtritter, K. Org. Lett. 2008, 10, 1325.
118. (a) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239.
119. (b) Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693.
120. Zarka, M. T.; Nuyken, O.; Weberskirch, R. Macromol. Rapid Commun. 2004, 25, 858.
121. Mingotaud, A.-F.; Krämer, M.; Mingotaud, C. J. Mol. Catal., A: Chem. 2007, 263, 39.
122. Gułajski, Ł.; Śledź, P.; Lupa, A.; Grela, K. Green Chem. 2008, 10, 271.
123. Gułajski, Ł.; Michrowska, A.; Narożnik, J.; Kaczmarska, Z.; Rupnicki, L.; Grela, K. ChemSusChem 2008, 1, 103.
124. Davis, K. J.; Sinou, D. J. Mol. Catal., A: Chem. 2002, 177, 173.
125. Lipshutz, B. H.; Ghorai, S.; Aguinaldo, G. T. Adv. Synth. Catal. 2008, 350, 953.
126. Lipshutz, B. H.; Ghorai, S.; Bošković, Ž. V. Tetrahedron 2008, 64, 6949.
127. Lipshutz, B. H.; Ghorai, S. University of California, Santa Barbara, CA. Unpublished work.
128. (a) Lipshutz, B. H.; Chung, D. W.; Rich, B. Org. Lett. 2008, 10, 3793.
129. (b) Gelman, D.; Buchwald, S. L. Angew. Chem., Int. Ed. 2003, 42, 5993.
130. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264.
131. Lipshutz, B. H.; Unger, J. B. University of California, Santa Barbara, CA. Unpublished work.
132. 10 in dietary supplements (Notice No. GRN 000202; http://www.cfsan.fda.gov/~rdb/opa-g202.html) , and has self-affirmed GRAS status for use as a food ingredient (accessed July 2008).