Investigating the nature of palladium chain-walking in the enantioselective redox-relay heck reaction of alkenyl alcohols

Journal of Organic Chemistry

Volumn 79, Issue 24, 2014, Pages 11841-11850

  Hilton, Margaret J ^a   Xu, Li Ping ^b   Norrby, Per Ola ^c   Wu, Yun Dong ^b   Wiest, Olaf ^b,d   Sigman, Matthew S ^a  

^a UNIVERSITY OF UTAH   (United States)

^b PEKING UNIVERSITY   (China)

^c ASTRAZENECA R AND D   (Sweden)

^d UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHAINS; CHEMICAL REACTIONS; DEUTERIUM; HYDRIDES; PALLADIUM; SUBSTRATES;

CHEMICAL EQUATIONS; ENANTIOSELECTIVE; HYDRIDE ELIMINATION; LABELED SUBSTRATES; MIGRATORY INSERTION; PRODUCT FORMATION; TAUTOMERIZATIONS; TRANSITION STRUCTURES;

ENANTIOSELECTIVITY;

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; ALKENYL GROUP; DEUTERIUM; PALLADIUM; ALKENE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; HECK REACTION; ISOMER; STEREOCHEMISTRY; TAUTOMERIZATION; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; QUANTUM THEORY; STEREOISOMERISM;

ALCOHOLS; ALKENES; CATALYSIS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM; QUANTUM THEORY; STEREOISOMERISM;

EID: 84919625245     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501813d     Document Type: Article

References (24)

1. Werner, E. W.; Mei, T.-S.; Burckle, A. J.; Sigman, M. S. Science 2012, 338, 1455.
2. Mei, T.-S.; Werner, E. W.; Burckle, A. J.; Sigman, M. S. J. Am. Chem. Soc. 2013, 135, 6830.
3. (a) Renata, H.; Zhou, Q.; Baran, P. S. Science 2013, 339, 59.
4. (b) Burns, N. Z.; Baran, P. S.; Hoffmann, R. W. Angew. Chem., Int. Ed. 2009, 48, 2854.
5. Milo, A.; Bess, E. N.; Sigman, M. S. Nature 2014, 507, 210.
6. Mei, T.-S.; Patel, H. H.; Sigman, M. S. Nature 2014, 508, 340.
7. Dang, Y.; Qu, S.; Wang, Z.-X.; Wang, X. J. Am. Chem. Soc. 2013, 136, 986.
8. Xu, L.; Hilton, M. J.; Zhang, X.; Norrby, P.-O.; Wu, Y.-D.; Sigman, M. S.; Wiest, O. J. Am. Chem. Soc. 2014, 136, 1960.
9. Tempel, D. J.; Johnson, L. K.; Huff, R. L.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 2000, 122, 6686.
10. Shultz, L. H.; Brookhart, M. Organometallics 2001, 20, 3975.
11. Shultz, L. H.; Tempel, D. J.; Brookhart, M. J. Am. Chem. Soc. 2001, 123, 11539.
12. Arnett, E. M. Prog. Phys. Org. Chem. 1963, 1, 223.
13. McMullin, C. L.; Jover, J.; Harvey, J. N.; Fey, N. Dalton Trans. 2010, 39, 10833-10836.
14. Willoughby, P. H.; Jansma, M. J.; Hoye, T. R. Nat. Protoc. 2014, 9 , 643.
15. Drent, E.; van Broekhoven, J. A. M.; Doyle, M. J. J. Organomet. Chem. 1991, 417, 235.
16. Zeng, J.; Deng, G.; Li, D. Biochim. Biophys. Acta, Gen. Subj. 2006, 1760, 78.
17. Hudrlik, P. F.; Hudrlik, A. M.; Yimenu, T.; Waugh, M. A.; Nagendrappa, G. Tetrahedron 1988, 44, 3791.
18. Luehr, G. W.; Arathi, S.; Jaishankar, P.; Bhakta, C.; Druzgala, P. PTC Int. Appl., 2010071813, Ed. 2010.
19. Kim, A. I.; Rychnovsky, S. D. Angew. Chem., Int. Ed. 2003, 42, 1267.
20. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215.
21. Frisch, M. J., et al. Gaussian Inc.: Wallingford, CT, 2009.
22. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993 , 208, 111.
23. Bell, R. P. The Tunnel Effect in Chemistry; Chapman and Hall: New York, 1980.
24. Legault, C. Y. http://www.cylview.org, Université de Sherbrooke, 2009.