Nickel-catalyzed Suzuki-Miyaura cross-coupling in a green alcohol solvent for an undergraduate organic chemistry laboratory

Journal of Chemical Education

Volumn 92, Issue 3, 2015, Pages 571-574

  Hie, Liana ^a   Chang, Jonah J ^a   Garg, Neil K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Green Chemistry; Hands On Learning Manipulatives; Heterocycles; Laboratory Instruction; Organic Chemistry; Organometallics; Second Year Undergraduate; Upper Division Undergraduate

Indexed keywords

EID: 84924406423     PISSN: 00219584     EISSN: 19381328     Source Type: Journal    
DOI: 10.1021/ed500158p     Document Type: Article

References (49)

1. Ashby, E. C. Grignard Reagents: Compositions and Mechanism of Reaction Q. Rev. Chem. Soc. 1967, 21 (2) 259-285
2. Ashby, E. C.; Laemmle, J.; Neumann, H. M. Mechanisms of Grignard Reagent Addition to Ketones Acc. Chem. Res. 1974, 7 (8) 272-280
3. Gore, P. H. The Friedel-Crafts Acylation Reaction and its Application to Polycyclic Aromatic Hydrocarbons Chem. Rev. 1955, 55 (2) 229-281
4. Groves, J. K. The Friedel-Crafts Acylation of Alkenes Chem. Soc. Rev. 1972, 1 (1) 73-97
5. th ed.; W. H. Freeman and Company: New York, 2014.
6. th ed.; Cengage Learning, Brooks/Cole Belmont: Cengage Learning, 2012.
7. nd ed.; Oxford University Press: New York, 2012.
8. Diederich, F.; de Meijere, A., Eds. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, 2004.
9. Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Aryl-Aryl Bond Formation One Century after the Discovery of the Ulmann Reaction Chem. Rev. 2002, 102 (5) 1359-1469
10. Miyaura, N., Ed. Topics in Current Chemistry, Vol. 219; Springer-Verlag: New York, 2002.
11. Corbet, J.-P.; Mignani, G. Selected Patented Cross-Coupling Reaction Technologies Chem. Rev. 2006, 106 (7) 2651-2710
12. Negishi, E. Transition Metal-Catalyzed Organometallic Reactions that Have Revolutionized Organic Synthesis Bull. Chem. Soc. Jpn. 2007, 80 (2) 233-257
13. Shen, H. C.; Crawley, M. L.; Trost, B. M., Eds.; Application of Transition Metal Catalysis in Drug Discovery and Development: An Industrial Perspective; John Wiley & Sons, Inc.: Hoboken, 2012.
14. Nobleprize.org: The Official Web Site of the Nobel Prize. The Nobel Prize in Chemistry 2010. http://www.nobelprize.org/nobel-prizes/chemistry/laureates/2010/ (accessed Aug 2014).
15. Costa, N. E.; Pelotte, A. L.; Simard, J. M.; Syvinski, C. A.; Deveau, A. M. Discovering Green, Aqueous Suzuki Coupling Reactions: Synthesis of Ethyl (4-Phenylphenyl)acetate, a Biaryl with Anti-Arthritic Potential J. Chem. Educ. 2012, 89 (8) 1064-1067
16. Aktoudianakis, E.; Chan, E.; Edward, A. R.; Jarosz, I.; Lee, V.; Mui, L.; Thatipamala, S. S.; Dicks, A. P. "Greening Up" the Suzuki Reaction J. Chem. Educ. 2008, 85 (4) 555-557
17. Hamilton, A. E.; Buxton, A. M.; Peeples, C. J.; Chalker, J. M. An Operationally Simple Aqueous Suzuki-Miyaura Cross-Coupling Reaction for an Undergraduate Organic Chemistry Laboratory J. Chem. Educ. 2013, 90 (11) 1509-1513
18. Callam, C. S.; Lowary, T. L. Suzuki Cross-Coupling Reactions: Synthesis of Unsymmetrical Biaryls in the Organic Laboratory J. Chem. Educ. 2001, 78 (7) 947-948
19. Hoogenboom, R.; Meier, M. A. R.; Schubert, U. S. The Introduction of High-Throughput Experimentation Methods for Suzuki-Miyaura Coupling Reactions in University Education J. Chem. Educ. 2005, 82 (11) 1693-1696
20. Herrmann, W. A.; Böhm, V. P. W.; Reisinger, C.-P. Introduction to Homogenous Catalysis: Carbon-Carbon Bond Formation Catalyzed by a Defined Palladium Complex J. Chem. Educ. 2000, 77 (1) 92-95
21. Dicks, A. P. Green Organic Laboratory in Lecture and Laboratory; CRC Press: Taylor & Franciss Group: Boca Raton, 2012.
22. Martin, R.; Buchwald, S. L. Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands Acc. Chem. Res. 2008, 41 (11) 1461-1473
23. Shan, F.-S. Transition-Metal-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions: a Remarkable Advance from Palladium to Nickel Catalysts Chem. Soc. Rev. 2013, 42 (12) 5270-5298
24. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds Chem. Rev. 1995, 95 (7) 2457-2483
25. Suzuki, A. Recent Advances in the Cross-Coupling Reactions of Organoboron Derivatives with Organic Electrophiles, 1995-1998 J. Organomet. Chem. 1999, 576 (1-2) 147-168
26. Dinges, J.; Lamberth, C., Eds. Bioactive Heterocyclic Compounds Classes: Pharmaceuticals; Wiley-VCH: Weinheim, 2012.
27. Quin, L. D.; Tyrell, J. Fundamentals of Heterocyclic Chemistry: Importance in Nature and in the Synthesis of Pharmaceuticals; Wiley-Interscience: Hoboken, 2010.
28. Alfonsi, K.; Colberg, J.; Dunn, P. J.; Fevig, T.; Jennings, S.; Johnson, T. A.; Kleine, H. P.; Knight, C.; Nagy, M. A.; Perry, D. A.; Stefaniak, M. Green Chemistry Tools to Influence a Medicinal Chemistry and Research Chemistry Organisation Green Chem. 2008, 10 (1) 31-36
29. Henderson, R. K.; Jiménez-González, C.; Constable, D. J. C.; Alston, S. R.; Inglis, G. G. A.; Fisher, G.; Sherwood, J.; Binks, S. P.; Curzons, A. D. Expanding GSK's Solvent Selection Guide-Embedding Sustainability into Solvent Selection Starting at Medicinal Chemistry Green Chem. 2011, 13 (4) 854-862
30. Prat, D.; Pardigon, O.; Flemming, H.-W.; Letestu, S.; Ducandas, V.; Isnard, P.; Guntrum, E.; Senac, T.; Ruisseau, S.; Cruciani, P.; Hosek, P. Sanofi's Solvent Selection Guide: A Step Toward More Sustainable Processes Org. Process Res. Dev. 2013, 17 (12) 1517-1525
31. Anastas, P. T.; Warner, J. C., Eds. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998.
32. Anastas, P. T.; Kirchhoff, M. M. Origins, Current Status, and Future Challenges of Green Chemistry Acc. Chem. Res. 2002, 35 (9) 686-694
33. For more information about the ACS Green Chemistry Institute Pharmaceutical Roundtable Solvent Selection Guide, see: http://www.acs.org/content/dam/acsorg/greenchemistry/industriainnovation/roundtable/solvent-selection-guide.pdf (accessed Aug 2014).
34. Fortunak, J. M. Current and Future Impact of Green Chemistry on the Pharmaceutical Industry Future Med. Chem. 2009, 1 (4) 571-575
35. Mesganaw, T.; Garg, N. K. Ni- and Fe-Catalyzed Cross-Coupling Reactions of Phenol Derivatives Org. Process. Res. Dev. 2013, 17, 29-39
36. Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.-N.; Garg, N. K.; Percec, V. Nickel-Catalyzed Cross-Couplings Involving Carbon-Oxygen Bonds Chem. Rev. 2011, 111 (3) 1346-1416
37. Hie, L.; Ramgren, S. D.; Mesganaw, T.; Garg, N. K. Nickel-Catalyzed Amination of Aryl Sulfamates and Carbamates Using an Air-Stable Precatalyst Org. Lett. 2012, 14 (16) 4182-4185
38. Ramgren, S. D.; Silberstein, A. L.; Yang, Y.; Garg, N. K. Nickel-Catalyzed Amination of Aryl Sulfamates Angew. Chem., Int. Ed. 2011, 50 (9) 2171-2173
39. Quasdorf, K. W.; Riener, M.; Petrova, K. V.; Garg, N. K. Suzuki-Miyaura Coupling of Aryl Carbamates, Carbonates, and Sulfamates J. Am. Chem. Soc. 2009, 131 (49) 17748-17749
40. Mesganaw, T.; Silberstein, A. L.; Ramgren, S. D.; Fine Nathel, N. F.; Hong, X.; Liu, P.; Garg, N. K. Nickel-Catalyzed Amination of Aryl Carbamates and Sequential Site-Selective Cross-Couplings Chem. Sci. 2011, 2 (9) 1766-1771
41. Quasdorf, K. W.; Tian, X.; Garg, N. K. Cross-Coupling Reactions of Aryl Pivalates with Boronic Acids J. Am. Chem. Soc. 2008, 130 (44) 14422-14423
42. Quasdorf, K. W.; Antoft-Finch, A.; Liu, P.; Silberstein, A. L.; Komaromi, A.; Blackburn, T.; Ramgren, S. D.; Houk, K. N.; Snieckus, V.; Garg, N. K. Suzuki-Miyaura Cross-Coupling of Aryl Carbamates and Sulfamates: Experimental and Computational Studies J. Am. Chem. Soc. 2011, 133 (16) 6352-6363
43. Fine Nathel, N. F.; Kim, J.; Hie, L.; Jiang, X.; Garg, N. K. Nickel-Catalyzed Amination of Aryl Chloride and Sulfamates in 2-Methyl-THF ACS Catal. 2014, 4 (9) 3289-3293
44. Berry, D. E.; Girard, S.; McAuley, A. The Synthesis and Reactions of Nickel(III) Stabilized by a Nitrogen-Donor Macrocycle J. Chem. Educ. 1996, 73 (6) 551-554
45. Birdwhistell, K. R.; Lanza, J. Simple Synthesis and Use of a Nickel Alkene Isomerization Catalyst. An Advanced Lab in Inorganic/Organometallic Chemistry J. Chem. Educ. 1997, 74 (5) 579-581
46. Alonso, F.; Yus, M. The Hydrogenation of Cyclododecene by Lithium Naphthalenide and Nickel Chloride Dihydrate J. Chem. Educ. 2001, 78 (11) 1517-1518
47. Pavlik, J. W. Catalytic Hydrogenation Using Nickel Boride J. Chem. Educ. 1972, 49 (8) 528
48. The commodity prices of Ni and Pd are estimated to be $6.46 USD/lb and $740.50 USD/oz, respectively. InvestmentMine: Mining Markets and Investment. http://www.infomine.com/investment/ (accessed Feb 2014).
49. Ramgren, S. D.; Hie, L.; Ye, Y.; Garg, N. K. Nickel-Catalyzed Suzuki-Miyaura Coupling in Green Solvents Org. Lett. 2013, 15 (15) 3950-3953