Organocatalytic synthesis of alkynes

Journal of the American Chemical Society

Volumn 137, Issue 32, 2015, Pages 10346-10350

  Zhang, Mengnan ^a   Jia, Tiezheng ^a   Wang, Carol Y ^a   Walsh, Patrick J ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CHEMICAL BONDS; FINANCIAL MARKETS; TRANSITION METALS;

CARBON-CARBON TRIPLE BONDS; CATALYTIC METHODS; DIVERSE MATERIALS; ELECTRONIC MATERIALS; FUNCTIONALIZATIONS; MEDICINAL CHEMISTRY; REACTION CONDITIONS; STOICHIOMETRIC REACTION;

HYDROCARBONS;

ALKYNE DERIVATIVE; BENZALDEHYDE DERIVATIVE; BENZYL CHLORIDE; HALIDE; STILBENE DERIVATIVE;

ARTICLE; BENZYLATION; CANNIZZARO REACTION; CATALYSIS; CATALYST; CROSS COUPLING REACTION; DIASTEREOISOMER; PROTON TRANSPORT; REACTION TIME; SONOGASHIRA REACTION; STEREOSPECIFICITY; STOICHIOMETRY; SYNTHESIS;

EID: 84939865430     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b06137     Document Type: Article

References (50)

1. Maiese, W. M.; Lechevalier, M. P.; Lechevalier, H. A.; Korshalla, J.; Kuck, N.; Fantini, A.; Wildey, M. J.; Thomas, J.; Greenstein, M. J. Antibiot. 1989, 42, 558 10.7164/antibiotics.42.558
2. Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285 10.1021/cr020085h
3. Muller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795 10.1021/cr0306788
4. Willis, M. C. Chem. Rev. 2010, 110, 725 10.1021/cr900096x
5. Godoi, B.; Schumacher, R. F.; Zeni, G. Chem. Rev. 2011, 111, 2937 10.1021/cr100214d
6. Gilmore, K.; Alabugin, I. V. Chem. Rev. 2011, 111, 6513 10.1021/cr200164y
7. Wille, U. Chem. Rev. 2013, 113, 813 10.1021/cr100359d
8. Salvio, R.; Moliterno, M.; Bella, M. Asian J. Org. Chem. 2014, 3, 340 10.1002/ajoc.201400021
9. Diederich, F.; Rubin, Y. Angew. Chem., Int. Ed. Engl. 1992, 31, 1101 10.1002/anie.199211013
10. Bunz, U. H. F.; Rubin, Y.; Tobe, Y. Chem. Soc. Rev. 1999, 28, 107 10.1039/a708900g
11. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769 10.1016/S0040-4039(01)94157-7
12. Michel, P.; Gennet, D.; Rassat, A. Tetrahedron Lett. 1999, 40, 8575 10.1016/S0040-4039(99)01830-4
13. Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1982, 47, 1837 10.1021/jo00349a007
14. Meffre, P.; Hermann, S.; Durand, P.; Reginato, G.; Riu, A. Tetrahedron 2002, 58, 5159 10.1016/S0040-4020(02)00438-6
15. Paquette, L. A.; Wittenbrook, L. S. J. Am. Chem. Soc. 1967, 89, 4483 10.1021/ja00993a042
16. Negishi, E.; King, A. O.; Klima, W. L.; Patterson, W.; Silveira, A. J. Org. Chem. 1980, 45, 2526 10.1021/jo01300a060
17. Cum, G.; Gallo, R.; Ipsale, S.; Spadaro, A. J. Chem. Soc., Chem. Commun. 1985, 1571 10.1039/c39850001571
18. Akiyama, S.; Tajima, K.; Nakatsuji, S.; Nakashima, K.; Abiru, K.; Watanabe, M. Bull. Chem. Soc. Jpn. 1995, 68, 2043 10.1246/bcsj.68.2043
19. Mandai, T.; Yanagi, T.; Araki, K.; Morisaki, T.; Kawada, M.; Otera, J. J. Am. Chem. Soc. 1984, 106, 3670 10.1021/ja00324a044
20. Orita, A.; Yoshioka, N.; Struwe, P.; Braier, A.; Beckmann, A.; Otera, J. Chem.-Eur. J. 1999, 5, 1355 10.1002/(SICI)1521-3765(19990401)5:4<1355::AID-CHEM1355>3.3.CO;2-S
21. Yang, L.-M.; Huang, L.-F.; Luh, T.-Y. Org. Lett. 2004, 6, 1461 10.1021/ol049686g
22. Verboom, W.; Westmijze, H.; Bos, H. J. T.; Vermeer, P. Tetrahedron Lett. 1978, 19, 1441 10.1016/S0040-4039(01)94568-X
23. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467 10.1016/S0040-4039(00)91094-3
24. Oh, C. H.; Jung, S. H. Tetrahedron Lett. 2000, 41, 8513 10.1016/S0040-4039(00)01543-4
25. Woon, E. C. Y.; Dhami, A.; Mahon, M. F.; Threadgill, M. D. Tetrahedron 2006, 62, 4829 10.1016/j.tet.2006.03.005
26. Zhang, W.; Moore, J. S. Adv. Synth. Catal. 2007, 349, 93 10.1002/adsc.200600476
27. Furstner, A. Angew. Chem., Int. Ed. 2013, 52, 2794 10.1002/anie.201204513
28. Goto, K.; Holler, M.; Okazaki, R. J. Am. Chem. Soc. 1997, 119, 1460 10.1021/ja962994s
29. Davis, F. A.; Jenkins, L. A.; Billmers, R. L. J. Org. Chem. 1986, 51, 1033 10.1021/jo00357a017
30. Goto, K.; Tokitoh, N.; Okazaki, R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1124 10.1002/anie.199511241
31. Griffiths, S. W.; King, J.; Cooney, C. L. J. Biol. Chem. 2002, 277, 25486 10.1074/jbc.M203089200
32. Poole, L. B.; Nelson, K. J. Curr. Opin. Chem. Biol. 2008, 12, 18 10.1016/j.cbpa.2008.01.021
33. Hall, A.; Karplus, P. A.; Poole, L. B. FEBS J. 2009, 276, 2469 10.1111/j.1742-4658.2009.06985.x
34. Paulsen, C. E.; Carroll, K. S. ACS Chem. Biol. 2010, 5, 47 10.1021/cb900258z
35. Jia, T.; Bellomo, A.; Montel, S.; Zhang, M.; Baina, K. E. L.; Zheng, B.; Walsh, P. J. Angew. Chem., Int. Ed. 2014, 53, 260 10.1002/anie.201307172
36. Jia, T.; Zhang, M.; Sagamanova, I. K.; Wang, C. Y.; Walsh, P. J. Org. Lett. 2015, 17, 1168 10.1021/acs.orglett.5b00092
37. Jia, T.; Bellomo, A.; El Baina, K.; Dreher, S. D.; Walsh, P. J. J. Am. Chem. Soc. 2013, 135, 3740 10.1021/ja4009776
38. O'donnell, J. S.; Schwan, A. L. J. Sulfur Chem. 2004, 25, 183 10.1080/1741599042000220761
39. Maitro, G.; Prestat, G.; Madec, D.; Poli, G. Tetrahedron: Asymmetry 2010, 21, 1075 10.1016/j.tetasy.2010.05.035
40. Schwan, A. L.; Soderman, S. C. Phosphorus, Sulfur Silicon Relat. Elem. 2013, 188, 275 10.1080/10426507.2012.729116
41. Maitro, G.; Vogel, S.; Sadaoui, M.; Prestat, G.; Madec, D.; Poli, G. Org. Lett. 2007, 9, 5493 10.1021/ol702343g
42. Soderman, S. C.; Schwan, A. L. J. Org. Chem. 2013, 78, 1638 10.1021/jo302769b
43. Izquierdo, F.; Chartoire, A.; Nolan, S. P. ACS Catal. 2013, 3, 2190 10.1021/cs400533e
44. Zong, L.; Ban, X.; Kee, C. W.; Tan, C.-H. Angew. Chem., Int. Ed. 2014, 53, 11849 10.1002/anie.201407512
45. Zhang, M.; Jia, T.; Yin, H.; Carroll, P. J.; Schelter, E. J.; Walsh, P. J. Angew. Chem., Int. Ed. 2014, 53, 10755 10.1002/anie.201405996
46. Schwan, A. L. ChemCatChem 2015, 7, 226 10.1002/cctc.201402817
47. Zhang, M.; Jia, T.; Sagamanova, I. K.; Pericas, M. A.; Walsh, P. J. Org. Lett. 2015, 17, 1164 10.1021/acs.orglett.5b00117
48. Muller, M.; Iyer, V. S.; Kubel, C.; Enkelmann, V.; Mullen, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1607 10.1002/anie.199716071
49. Kingsbury, C. A.; Auerbach, R. A. J. Org. Chem. 1971, 36, 1737 10.1021/jo00812a003
50. Kingsbury, C. A. J. Org. Chem. 1972, 37, 102 10.1021/jo00966a028