銅鹽作用下，吡啶和芐基鹵代物反應(yīng)得到2位或4位芐基化產(chǎn)物的反應(yīng)。其他的一些烷基鹵代物也可以進(jìn)行此反應(yīng)，但產(chǎn)率不高。
反應(yīng)機(jī)理
銅鹽催化下的自由基機(jī)理
反應(yīng)操作
Benzylpyridines (3) and (4). Pyr hydrochloride 1 (462 g, 4 mol), CuCl2 (5 g, 37 mmol) and Pyr (60 mL) were treated with benzyl chloride 2 (126.5 g, 115 mL, 1 mol) and refluxed for 12 h. The mixture was distilled until the temperature reached 195 C. The cooled residue was treated with water (200 mL) and 32% HCl (15 mL), stirred until homogeneous and made alkaline with 25% NH4OH.
Extraction with PE: PhH, washing the extract with NH4OH and evaporation afforded a mixture of 3 and 4, bp 123–125 ℃ and 175–190 ℃.
【Croock KE, J Am Chem Soc., 1948, 70, 416】
相關(guān)文獻(xiàn)
1 Ladenburg A Liebig’s Ann 1883 16 1410
2 Croock KE J Am Chem Soc 1948 70 416
3R Brewster JH Org React 1953 7 135
4 Yoh SD J Phy Org Chem 2001 14 123
5 Radix S Tet Lett 2009 50 1828
6 Ackermann L Org Lett 2009 11 4966
編譯自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 279.
