Nickel-catalyzed Negishi arylations of propargylic bromides: A mechanistic investigation

Journal of the American Chemical Society

Volumn 136, Issue 47, 2014, Pages 16588-16593

  Schley, Nathan D ^a   Fu, Gregory C ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COUPLINGS;

ARYLATIONS; CROSS-COUPLINGS; ELECTROPHILES; ENANTIOSELECTIVE; MECHANISTIC STUDIES; ORGANIC CHEMISTRY; OXIDATIVE ADDITIONS; RADICAL CHAIN;

NICKEL;

ALKYL GROUP; ARYLNICKEL(II) COMPLEX; BROMINE DERIVATIVE; CARBON; ELECTROPHILE; NICKEL COMPLEX; RADICAL; UNCLASSIFIED DRUG; ALKANE; NICKEL; PARGYLINE; PROPARGYL BROMIDE;

ARTICLE; ARYLATION; CATALYST; CHEMICAL BOND; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; OXIDATIVE COUPLING; RACEMIC MIXTURE; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY; ANALOGS AND DERIVATIVES; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALKANES; CATALYSIS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NICKEL; OXIDATION-REDUCTION; PARGYLINE;

EID: 84913539477     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja508718m     Document Type: Article

References (26)

1. For reviews and leading references, see: Science of Synthesis: Cross-Coupling and Heck-Type Reactions; Molander, G. A., Ed.; Georg Thieme Verlag: Stuttgart, 2013.
2. For a recent overview, see: Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299-309
3. For an earlier overview, see: Modern Organonickel Chemistry; Tamaru, Y., Ed.; Wiley-VCH: Weinheim, 2005.
4. For leading references to mechanistic work on nickel-catalyzed cross-couplings of alkyl electrophiles, see: Hu, X. Chem. Sci. 2011, 2, 1867-1886
5. Initial report: Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 14726-14727
6. Initial report of stereoconvergent reactions: Fischer, C.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 4594-4595
7. Most recent report of stereoconvergent reactions: Choi, J.; Martín-Gago, P.; Fu, G. C. J. Am. Chem. Soc. 2014, 136, 12161-12165
8. Glasspoole, B. W.; Crudden, C. M. Nat. Chem. 2011, 3, 912-913
9. Geist, E.; Kirschning, A.; Schmidt, T. Nat. Prod. Rep. 2014, 31, 441-448
10. Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 1340-1341
11. Powell, D. A.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 7788-7789
12. For a review of radical reactions catalyzed by Group 10 metals, see: Jahn, U. Top. Curr. Chem. 2012, 320, 323-451
13. Jones, G. D.; Martin, J. L.; McFarland, C.; Allen, O. R.; Hall, R. E.; Haley, A. D.; Brandon, R. J.; Konovalova, T.; Desrochers, P. J.; Pulay, P.; Vicic, D. A. J. Am. Chem. Soc. 2006, 128, 13175-13183
14. Lin, X.; Phillips, D. L. J. Org. Chem. 2008, 73, 3680-3688
15. Biswas, S.; Weix, D. J. J. Am. Chem. Soc. 2013, 135, 16192-16197
16. Breitenfeld, J.; Ruiz, J.; Wodrich, M. D.; Hu, X. J. Am. Chem. Soc. 2013, 135, 12004-12012
17. See also: Zheng, B.; Tang, F.; Luo, J.; Schultz, J. W.; Rath, N. P.; Mirica, L. M. J. Am. Chem. Soc. 2014, 136, 6499-6504
18. Lin, X.; Sun, J.; Xi, Y.; Lin, D. Organometallics 2011, 30, 3284-3292
19. This study by Lin examines the cross-coupling developed in: Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 10482-10483.
20. Smith, S. W.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 12645-12647
21. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877-910
22. For a report of a pyridine-2,6-diimine serving as a redox-active ligand, see: de Bruin, B.; Bill, E.; Bothe, E.; Weyhermüller, T.; Wieghardt, K. Inorg. Chem. 2000, 39, 2936-2947
23. Luca, O. R.; Crabtree, R. H. Chem. Soc. Rev. 2013, 42, 1440-1459
24. Praneeth, V. K. K.; Ringenberg, M. R.; Ward, T. R. Angew. Chem., Int. Ed. 2012, 51, 10228-10234
25. Lyaskovskyy, V.; de Bruin, B. ACS Catal. 2012, 2, 270-279
26. Newcomb, M. Tetrahedron 1993, 49, 1151-1176