Fujiwara镧系金属催化反应
2020-10-28 01:10:50   来源:

芳香酮或芳香卤代物与镧系金属(如镱,Yb)络合后,对酮,腈,环氧化物和卤代物等进行亲核加成或亲核取代的反应。

酮与镧系金属的络合物与腈反应得到α-羟基酮。

2-Oxo-1,1,3-triphenylpropan-1-ol (6). Yb powder (173 mg, 1 mmol) under N2 was treated with a drop of MeI and was heated to activate the Yb. THF (2 mL) was added, followed by HMPA (1 mL). Under stirring benzophenone 1 (182 mg, 1 mmol) in THF (2 mL) was added, followed by phenylacetonitrile 5 (117 mg, 1 mmol). After 4 h stirring at 20 C, the mixture was quenched with 2N HCl, extracted with Et2O and the product separated by medium pressure LC to afford 187 mg of 6 (65%) and 50 mg of 4 (35%).

【Fujiwara Y, J Org Chem1988, 53, 6077】

酮与镧系金属的络合物与环氧化合物反应得到1,3-二醇。

芳香卤代物与镧系金属反应络合得到类似格氏试剂的络合物,可以和卤代物进行取代反应。

取代反应

【Su W, Tet Lett2002, 43, 2251】

相关文献

1 Fujiwara Y Chem Lett 1981 1771

2 Fujiwara Y J Org Chem 1984 49 3237

3 Fujiwara Y J Org Chem 1987 52 3524

4 Fujiwara Y J Org Chem 1988 53 6077

5 Su W Tet Lett 2002 43 2251

编译自:Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 170-171.

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