Revelation of the difference between arylzinc reagents prepared from aryl grignard and aryllithium reagents respectively: Kinetic and structural features

Journal of the American Chemical Society

Volumn 131, Issue 46, 2009, Pages 16656-16657

  Jin, Liqun ^a   Liu, Chao ^a,c   Liu, Jing ^a   Hu, Fang ^a   Lan, Yu ^a   Batsanov, Andrei S ^c   Howard, Judith A K ^c   Marder, Todd B ^c   Lei, Aiwen ^a,b  

^a WUHAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLZINC REAGENTS; CATALYTIC REACTIONS; DFT CALCULATION; FIRST ORDER KINETICS; GRIGNARD; KINETIC BEHAVIOR; RATE LIMITING; RATE-LIMITING STEPS; SINGLE CRYSTAL X-RAY DIFFRACTION ANALYSIS; SOLUTION NMR; STRUCTURAL FEATURE; TRANSMETALATION; ZERO ORDER KINETICS;

CATALYSIS; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLICS; SULFUR COMPOUNDS; ZINC;

X RAY DIFFRACTION ANALYSIS;

GRIGNARD REAGENT; LITHIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; KINETICS; OXIDATION; X RAY DIFFRACTION;

EID: 70450186031     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja908198d     Document Type: Article

References (29)

1. de Meijere, A., Diederich, F., Eds. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; Wiley-VCH: Weinheim, 2004; Vol.2.
2. Negishi, E.; King, A. O.; Okukado, N. J. Org. Chem. 1977, 42, 1821-1823.
3. King, A. O.; Negishi, E.; Villani, F. J., Jr.; Silveira, A., Jr. J. Org. Chem. 1978, 43, 358-360.
4. Negishi, E.-I. In Organozinc Reagents: A Practical Approach; Knochel P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; pp 213-243.
5. Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Lin, S.-C.; Li, L.; Fukuyama, T. J. Braz. Chem. Soc. 1998, 9, 381-387.
6. Zhao, Y.; Wang, H.; Hou, X.; Hu, Y.; Lei, A.; Zhang, H.; Zhu, L. J. Am. Chem. Soc. 2006, 128, 15048-15049.
7. Jin, L.; Zhao, Y.; Wang, H.; Lei, A. Synthesis 2008, 649-654.
8. Knochel, P., Jones, P., Eds. Organozinc Reagents: A Practical Approach; Oxford University Press: Oxford, 1999.
9. Knochel, P.; Jones, P.; Langer, F. In Organozinc Reagents: A Practical Approach; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, 1999; pp 1-21.
10. Salvi, L.; Kim, J. G.; Walsh, P. J. J. Am. Chem. Soc. 2009, 131, 12483-12493.
11. Rohbogner, C. J.; Wunderlich, S. H.; Clososki, G. C.; Knochel, P. Eur. J. Org. Chem. 2009, 1781-1795.
12. Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333-3336.
13. Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 10482-10483.
14. Lundin, P. M.; Esquivias, J.; Fu, G. C. Angew. Chem., Int. Ed. 2009, 48, 154-156.
15. Fischer, C.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 4594-4595.
16. Smith, S. W.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 12645-12647.
17. 2Zn: Casares, J. A.; Espinet, P.; Fuentes, B.; Salas, G. J. Am. Chem. Soc. 2007, 129, 3508-3509.
18. Liu, Q.; Lan, Y.; Liu, J.; Li, G.; Wu, Y.-D.; Lei, A. J. Am. Chem. Soc. 2009, 131, 10201-10210.
19. Jin, L.; Zhang, H.; Li, P.; Sowa, J. R.; Lei, A. J. Am. Chem. Soc. 2009, 131, 9892-9893.
20. Mathew, J. S.; Klussmann, M.; Iwamura, H.; Valera, F.; Futran, A.; Emanuelsson, E. A. C.; Blackmond, D. G. J. Org. Chem. 2006, 71, 4711-4722.
21. The mechanism of this oxidative coupling was proposed to include oxidative addition of desyl chloride to [Ni], transmetalation, and reductive elimination. If oxidative addition was rate-limiting, the reaction would be first-order in [desyl chloride]. If reductive elimination was rate-limiting, the reaction rate would be independent of [desyl chloride] and [aryl zinc]. See ref 19.
22. The detailed comparison is as follows: TM (1a) ≫ RE (1a), TM (1b) ≪ RE (1b), RE (1a) = RE (1b). Thus, TM(1a) ≫ TM(1b). TM: rate of transmetalation step. RE: rate of reductive elimination step.
23. 2 was stirred for 2 h before the addition of desyl chloride and Ni-catalyst.
24. Zhu, Z.; Brynda, M.; Wright, R. J.; Fischer, R. C.; Merrill, W. A.; Rivard, E.; Wolf, R.; Fettinger, J. C.; Olmstead, M. M.; Power, P. P. J. Am. Chem. Soc. 2007, 129, 10847-10857.
25. Wang, Y.; Quillian, B.; Wannere, C. S.; Wei, P.; Schleyer, P. v. R.; Robinson, G. H. Organometallics 2007, 26, 3054-3056.
26. Sarazin, Y.; Wright, J. A.; Harding, D. A. J.; Martin, E.; Woodman, T. J.; Hughes, D. L.; Bochmann, M. J. Organomet. Chem. 2008, 693, 1494-1501.
27. Chua, J.; Garcia-Alvarez, P.; McCall, M. D.; Hevia, E. presented at the RSC Conference on Main Group Chemistry, Manchester, September 11, 2009.
28. There is clearly a dynamic process, but only the ipso C and ortho H resonances are significantly affected by temperature.
29. 2 facilitates the transmetalation and corresponding DFT calculations for this process are ongoing in this laboratory and will be reported in due course.