Samarium in organic synthesis. I. reaction of allyl or benzyl halides with carbonyl compounds promoted by samarium metal

Acta Chimica Sinica ›› 1993, Vol. 51 ›› Issue (11): 1139-1144. Previous Articles

Original Articles

钐试剂在合成中的应用I. 金属钐作用下烯丙基和苄基卤代物与羰基化合物的反应

王翔;蔡瑞芳;卫景德;高翔;吴世晖

复旦大学化学系;南开大学元素有机化学国家重点实验室

发布日期:1993-11-15

Samarium in organic synthesis. I. reaction of allyl or benzyl halides with carbonyl compounds promoted by samarium metal

WANG XIANG;CAI RUIFANG;WEI JINGDE;GAO XIANG;WU SHIHUI

Published:1993-11-15

Abstract

Samarium metal promoted Barbier-type reactions have been investigated. Samarium metal (activated by HgCl2) is an effective reagent for allylation or benzylation of ketones. The corresponding tertiary alcs. are obtained in satisfactory yields. This reaction is regioselective and chemoselective. When reaction with a,b-unsatd. ketones no. 1,4-addn. products were found. The reactive groups (such as Br, Cl and methoxyl) or aromatic ketones in this reaction condition remain unchanged. An organosamarium intermediate reaction mechanism has been suggested.

Key words: CARBONYL COMPOUNDS, ORGANIC SYNTHESIS, ALLYL GROUP, ARYL HALIDE

CLC Number:

O621

Cite this article

WANG XIANG;CAI RUIFANG;WEI JINGDE;GAO XIANG;WU SHIHUI. Samarium in organic synthesis. I. reaction of allyl or benzyl halides with carbonyl compounds promoted by samarium metal[J]. Acta Chimica Sinica, 1993, 51(11): 1139-1144.

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钐试剂在合成中的应用I. 金属钐作用下烯丙基和苄基卤代物与羰基化合物的反应

Samarium in organic synthesis. I. reaction of allyl or benzyl halides with carbonyl compounds promoted by samarium metal

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