Soft propargylic deprotonation: Designed ligand enables au-catalyzed isomerization of alkynes to 1,3-Dienes

Journal of the American Chemical Society

Volumn 136, Issue 25, 2014, Pages 8887-8890

  Wang, Zhixun ^a   Wang, Yanzhao ^a   Zhang, Liming ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOMERIZATION; ISOMERS;

1 ,3-DIENES; AMINO GROUP; DESIGN LEDS; GOLD COMPLEXES; MILD REACTION CONDITIONS; PROTONATED;

OLEFINS;

1,3 DIENE; ALKADIENE; ALKYNE DERIVATIVE; ANILINE; CARBONYL DERIVATIVE; DIMETHYL SULFOXIDE; GOLD COMPLEX; HYDROGEN; LIGAND; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG; ALKYNE; GOLD; PROTON;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERIZATION; LIGAND BINDING; REACTION ANALYSIS; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

ALKADIENES; ALKYNES; CATALYSIS; GOLD; LIGANDS; MOLECULAR CONFORMATION; PROTONS; STEREOISOMERISM;

EID: 84903287314     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja503909c     Document Type: Article

References (24)

1. Thirsk, C.; Whiting, A. J. Chem. Soc. Perk. Trans. 1 2002, 0, 999
2. Taylor, R. E.; Diene, C. R.; Daly, E. M. Sci. Synth. 2009, 46, 571
3. Guo, C.; Lu, X. Tetrahedron Lett. 1991, 32, 7549
4. Trost, B. M.; Schmidt, T. J. Am. Chem. Soc. 1988, 110, 2301
5. Kwong, C. K.-W.; Fu, M. Y.; Lam, C. S.-L.; Toy, P. H. Synthesis 2008, 2008, 2307
6. Shintani, R.; Duan, W.-L.; Park, S.; Hayashi, T. Chem. Commun. 2006, 3646
7. Yasui, H.; Yorimitsu, H.; Oshima, K. Synlett 2006, 2006, 1783
8. Otera, J. Modern Carbonyl Chemistry; Wiley-VCH: Weinheim, 2000.
9. Rathke, M. W.; Cowan, P. J. J. Org. Chem. 1985, 50, 2622
10. Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624
11. Tirpak, R. E.; Olsen, R. S.; Rathke, M. W. J. Org. Chem. 1985, 50, 4877
12. Ren, J.; Cramer, C. J.; Squires, R. R. J. Am. Chem. Soc. 1999, 121, 2633
13. Robinson, M. S.; Polak, M. L.; Bierbaum, V. M.; DePuy, C. H.; Lineberger, W. C. J. Am. Chem. Soc. 1995, 117, 6766
14. Matthews, W. S.; Bares, J. E.; Bartmess, J. E.; Bordwell, F. G.; Cornforth, F. J.; Drucker, G. E.; Margolin, Z.; McCallum, R. J.; McCollum, G. J.; Vanier, N. R. J. Am. Chem. Soc. 1975, 97, 7006
15. Fors, B. P.; Watson, D. A.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 13552
16. Billingsley, K.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3358-3366
17. Anderson, K. W.; Tundel, R. E.; Ikawa, T.; Altman, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 6523
18. Mauger, C. C.; Mignani, G. A. Aldrichimica Acta 2006, 39, 17
19. Schlummer, B.; Scholz, U. Adv. Synth. Catal. 2004, 346, 1599
20. Lee, H. G.; Milner, P. J.; Buchwald, S. L. J. Am. Chem. Soc. 2014, 136, 3792-3795
21. Anderson, K. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2005, 44, 6173
22. Nieto-Oberhuber, C.; Lopez, S.; Munoz, M. P.; Cardenas, D. J.; Bunuel, E.; Nevado, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2005, 44, 6146
23. Wang, Y.; Wang, Z.; Li, Y.; Wu, G.; Cao, Z.; Zhang, L. Nat. Commun. 2014, 5, doi: 10.1038/ncomms4470.
24. Khin, C.; Hashmi, A.S. K.; Rominger, F. Eur. J. Inorg. Chem. 2010, 2010, 1063