NHC-stabilized triorganozincates: Syntheses, structures, and transformation to abnormal carbene-zinc complexes

Angewandte Chemie - International Edition

Volumn 51, Issue 40, 2012, Pages 10173-10176

  Wang, Yuzhong ^a   Xie, Yaoming ^a   Abraham, Mariham Y ^a   Gilliard, Robert J ^a   Wei, Pingrong ^a   Campana, Charles F ^b   Schaefer III, Henry F ^a   Schleyer, Paul Von R ^a   Robinson, Gregory H ^a  

^a UNIVERSITY OF GEORGIA   (United States)

^b BRUKER AXS INC   (United States)

Author keywords

abnormal carbenes; density functional calculations; N heterocyclic carbenes; zinc; zincates

Indexed keywords

ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL); ZINC COMPOUNDS;

ABNORMAL CARBENE; CARBENES; COMPLEX GAPS; DENSITY-FUNCTIONAL CALCULATIONS; N-HETEROCYCLIC CARBENES; SYNTHESISED; TRINUCLEAR; ZINC COMPLEX; ZINCATE;

DENSITY FUNCTIONAL THEORY;

EID: 84867031426     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201204712     Document Type: Article

References (47)

1. M. Uchiyama, S. Furumoto, M. Saito, Y. Kondo, T. Sakamoto, J. Am. Chem. Soc. 1997, 119, 11425-11433.
2. M. Uchiyama, S. Nakamura, T. Ohwada, M. Nakamura, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 10897-10903.
3. D. J. Linton, P. Schooler, A. E. H. Wheatley, Coord. Chem. Rev. 2001, 223, 53-115.
4. A. E. H. Wheatley, New J. Chem. 2004, 28, 435-443.
5. Z. Rappoport, I. Marek, The Chemistry of Organozinc Compounds: R-Zn, Wiley, Chichester, 2006, pp. 31-135.
6. R. E. Mulvey, F. Mongin, M. Uchiyama, Y. Kondo, Angew. Chem. 2007, 119, 3876-3899
7. Angew. Chem. Int. Ed. 2007, 46, 3802-3824.
8. R. E. Mulvey, Organometallics 2006, 25, 1060-1075.
9. R. E. Mulvey, Acc. Chem. Res. 2009, 42, 743-755.
10. M. Uchiyama, M. Koike, M. Kameda, Y. Kondo, T. Sakamoto, J. Am. Chem. Soc. 1996, 118, 8733-8734.
11. M. Uchiyama, M. Kameda, O. Mishima, N. Yokoyama, M. Koike, Y. Kondo, T. Sakamoto, J. Am. Chem. Soc. 1998, 120, 4934-4946.
12. T. Furuyama, M. Yonehara, S. Arimoto, M. Kobayashi, Y. Matsumoto, M. Uchiyama, Chem. Eur. J. 2008, 14, 10348-10356.
13. M. Uchiyama, T. Furuyama, M. Kobayashi, Y. Matsumoto, K. Tanaka, J. Am. Chem. Soc. 2006, 128, 8404-8405.
14. A. R. Kennedy, J. Klett, R. E. Mulvey, D. S. Wright, Science 2009, 326, 706-708.
15. R. Campbell, P. Garcia-Alvarez, A. R. Kennedy, R. E. Mulvey, Chem. Eur. J. 2010, 16, 9964-9968.
16. R. Campbell, D. Cannon, P. Garcia-Alvarez, A. R. Kennedy, R. E. Mulvey, S. D. Robertson, J. Sassmannshausen, T. Tuttle, J. Am. Chem. Soc. 2011, 133, 13706-13717.
17. S. P. Nolan, N-Heterocyclic Carbenes in Synthesis, Wiley-VCH, Weinheim, 2006.
18. Y. Wang, G. H. Robinson, Chem. Commun. 2009, 5201-5213.
19. Y. Wang, G. H. Robinson, Inorg. Chem. 2011, 50, 12326-12337.
20. Y. Wang, G. H. Robinson, Dalton Trans. 2012, 41, 337-345.
21. D. Martin, M. Melaimi, M. Soleilhavoup, G. Bertrand, Organometallics 2011, 30, 5304-5313.
22. D. Martin, M. Soleilhavoup, G. Bertrand, Chem. Sci. 2011, 2, 389-399.
23. S.-L. Yao, Y. Xiong, M. Driess, Organometallics 2011, 30, 1748-1767.
24. R. Jensen Tryg, E. Breyfogle Laurie, A. Hillmyer Marc, B. Tolman William, Chem. Commun. 2004, 2504-2505.
25. T. R. Jensen, C. P. Schaller, M. A. Hillmyer, W. B. Tolman, J. Organomet. Chem. 2005, 690, 5881-5891.
26. B. Bantu, G. Manohar Pawar, K. Wurst, U. Decker, A. M. Schmidt, M. R. Buchmeiser, Eur. J. Inorg. Chem. 2009, 1970-1976.
27. P. L. Arnold, I. J. Casely, Z. R. Turner, R. Bellabarba, R. B. Tooze, Dalton Trans. 2009, 7236-7247.
28. P. L. Arnold, S. Pearson, Coord. Chem. Rev. 2007, 251, 596-609.
29. O. Schuster, L. Yang, H. G. Raubenheimer, M. Albrecht, Chem. Rev. 2009, 109, 3445-3478.
30. Y. Wang, Y. Xie, M. Y. Abraham, P. Wei, H. F. Schaefer III, P. v. R. Schleyer, G. H. Robinson, J. Am. Chem. Soc. 2010, 132, 14370-14372.
31. Y. Wang, Y. Xie, M. Y. Abraham, P. Wei, H. F. Schaefer III, P. v. R. Schleyer, G. H. Robinson, Organometallics 2011, 30, 1303-1306.
32. Y. Wang, M. Y. Abraham, R. J. Gilliard, Jr., P. Wei, J. C. Smith, G. H. Robinson, Organometallics 2012, 31, 791-793.
33. 2), 886574 (3 ·TMEDA), 886575 (4), 886576 (5) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
34. Computations: The structure of the simplified model compound 2 a was optimized at the B3LYP/DZP DFT level with the Gaussian 94 and Gaussian 03 programs: M. J. Frisch, et al. Gaussian 94, Revision B.3; Gaussian Inc.: Pittsburgh, PA, 1995; Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004. See the Supporting Information for the full citations.
35. G. Anantharaman, K. Elango, Organometallics 2007, 26, 1089-1092.
36. A. J. Arduengo III, H. V. R. Dias, F. Davidson, R. L. Harlow, J. Organomet. Chem. 1993, 462, 13-18.
37. M. Albrecht, Chem. Commun. 2008, 3601-3610.
38. S. Gründemann, A. Kovacevic, M. Albrecht, J. W. Faller, R. H. Crabtree, Chem. Commun. 2001, 2274-2275.
39. E. Aldeco-Perez, A. J. Rosenthal, B. Donnadieu, P. Parameswaran, G. Frenking, G. Bertrand, Science 2009, 326, 556-559.
40. M. Melaimi, M. Soleilhavoup, G. Bertrand, Angew. Chem. 2010, 122, 8992-9032
41. Angew. Chem. Int. Ed. 2010, 49, 8810-8849.
42. D. Mendoza-Espinosa, B. Donnadieu, G. Bertrand, J. Am. Chem. Soc. 2010, 132, 7264-7265.
43. T. W. Graham, K. A. Udachin, A. J. Carty, Chem. Commun. 2006, 2699-2701.
44. D. Holschumacher, T. Bannenberg, C. G. Hrib, P. G. Jones, M. Tamm, Angew. Chem. 2008, 120, 7538-7542
45. Angew. Chem. Int. Ed. 2008, 47, 7428-7432.
46. D. Holschumacher, T. Bannenberg, K. Ibrom, C. G. Daniliuc, P. G. Jones, M. Tamm, Dalton Trans. 2010, 39, 10590-10592.
47. C. A. Reed, Acc. Chem. Res. 2010, 43, 121-128.