Palladium-catalyzed highly regio- and stereoselective synthesis of (1E)- or (1Z)-1,2-dihalo-1,4-dienes via haloallylation of alkynyl halides

Palladium-catalyzed highly regio- and stereoselective synthesis of (1E)- or (1Z)-1,2-dihalo-1,4-dienes via haloallylation of alkynyl halides
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钯催化通过炔基卤化物的卤代烯丙基化高度区域和立体选择性合成 (1E)- 或 (1Z)-1,2-二卤-1,4-二烯

DOI:
10.1039/c0cc04879h
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发表时间:
2011-01-01
影响因子:
4.9
通讯作者:
Zhu, Gangguo
Zhu, Gangguo
中科院分区:
化学2区
文献类型:
--
作者:
Chen, Xiaoyi;Kong, Wei;Zhu, Gangguo

文献摘要

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本发明描述了一种通过钯催化的卤代炔和烯丙基卤化物的偶联高效和选择性地合成(1 E)-或(1 Z)-1,2-二卤代-1,4-二烯的方法。(1 E)-1,2-二卤-1,4-二烯以良好的产率和优异的立体选择性(1 E/1 Z高达> 98/2)生成,而(1 Z)-1,2-二卤-1,4-二烯通过简单地加入化学计量的卤化锂以优异的产率和立体选择性(1 Z/1 E高达> 98/2)生成。
A highly efficient and selective synthesis of (1E)- or (1Z)-1,2-dihalo-1,4-dienes via Pd-catalyzed coupling of haloalkynes and allylic halides is described. The (1E)-1,2-dihalo-1,4-dienes were generated in good yields with excellent stereoselectivities (1E/1Z up to > 98/2), while (1Z)-1,2-dihalo-1,4-dienes were produced in excellent yields and stereoselectivities (1Z/1E up to > 98/2) by simply adding stoichiometric lithium halides.