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2010年诺贝尔化学奖早就公布了,关于化学奖得主的丰功伟绩我就不再累赘了,在此我将以三个人人名命名化学反应及其机理罗列出来,请看:http://news.sciencenet.cn/htmlnews/2010/10/238373.shtm。详细的有机人名反应及其机理请看我的博文:http://www.sciencenet.cn/m/user_content.aspx?id=13050。
1、Heck Reaction
R. F. Heck, J. P. Nolley, Jr., J. Org. Chem. 37, 2320 (1972).
Stereospecific palladium-catalyzed coupling of alkenes with organic halides or triflates lacking sp3-hybridized β-hydrogens:
Variation of reaction parameters in the context of the asymmetric synthesis of (+)-vernolepin: K. Ohrai et al., J. Am. Chem. Soc. 116, 11737 (1994). Review of intramolecular reactions: L. E. Overman, Pure Appl. Chem. 66, 1423-1430 (1994); S. E. Gibson et al., Contemp. Org. Syn. 3, 447-471 (1996); J. T. Link, L. E. Overman, Met.-Catal. Cross-Coupling React. 1998, 231-269. Reviews: R. F. Heck, Org. React. 27, 345-390 (1982); A. de Meijere, F. E. Meyer, Angew. Chem. Int. Ed. 33, 2379-2411 (1994); W. Cabri, I. Candiani, Accts. Chem. Res. 28, 2-7 (1995). Review of mechanism: G. T. Crisp, Chem. Soc. Rev. 27, 427-436 (1998); of enantioselective syntheses: M. Shibasaki, E. M. Vogl, J. Organometal. Chem. 576, 1-15 (1999); O. Loiseleur et al., ibid. 16-22; U. Iserloh, D. P. Curran, Chemtracts 12, 289-296 (1999). Cf. Stille Coupling; Suzuki Coupling.
2、Negishi Cross Coupling
E. Negishi et al., J. Org. Chem. 42, 1821 (1977).
Formation of unsymmetric biaryls by cross coupling arylhalides with arylzinc reagents in presence of catalytic Ni or Pd:
Synthetic application: S. Superchi et al., Tetrahedron Letters 37, 6057 (1996); J. A. Miller, R. P. Farrell, ibid. 39, 6441 (1998). Extension to additional functional groups: E. Negishi, Acc. Chem. Res. 15, 340 (1982). Review: P. Knochel, R. D. Singer, Chem. Rev. 93, 2117-2188 (1993); idem et al., Ber. 130, 1021-1027 (1997).
3、Suzuki Coupling
N. Miyaura et al., Tetrahedron Letters 1979, 3437; N. Miyaura, A. Suzuki, Chem. Commun. 1979, 866.
Palladium-catalyzed cross coupling of organic halides or perfluorinated sulfonates with organoboron derivatives proceeding with high stereo- and regioselectivity:
Competition with Heck reaction, q.v., when using an alkenyl boronate ester: A. R. Hunt et al., Tetrahedron Letters 34, 3599 (1993). Alternative palladium catalysts: G. Marck et al., ibid. 35, 3277 (1994); T. I. Wallow, B. M. Novak, J. Org. Chem. 59, 5034 (1994). Reviews: A. Suzuki, Pure Appl. Chem. 63, 419-422 (1991); A. R. Martin, Y. Yang, Acta Chem. Scand. 47, 221-230 (1993). Cf. Hydroboration Reaction; Stille Coupling.
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