Pd-Catalyzed Asymmetric Alkylation of Methylphenylphosphine with Alkyl Halides for the Synthesis of P-stereogenic Compounds

doi:10.6023/cjoc201301050

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (04): 799-802.DOI: 10.6023/cjoc201301050 Previous Articles Next Articles

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钯催化甲基苯基膦氢的不对称烷基化反应合成含膦手性中心化合物

李春^a, 李伟逊^b, 许胜^a, 段伟良^b

a 华东理工大学化学与分子工程学院上海 200237;
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

收稿日期:2013-01-21 修回日期:2013-02-26 发布日期:2013-03-01
通讯作者: 许胜, 段伟良 E-mail:wlduan@mail.sioc.ac.cn
基金资助:
国家重点基础研究发展计划(973计划, No. 2010CB833300)、国家自然科学基金(Nos. 20902099, 21172238)、中国科学院上海有机化学研究所启动经费资助项目.

Pd-Catalyzed Asymmetric Alkylation of Methylphenylphosphine with Alkyl Halides for the Synthesis of P-stereogenic Compounds

Li Chun^a, Li Weixun^b, Xu Sheng^a, Duan Weiliang^b

a School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237;
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2013-01-21 Revised:2013-02-26 Published:2013-03-01
Supported by:
Project supported by the National Basic Research Program of China (973 Program, 2010CB833300), the National Natural Science Foundation of China (Nos. 20902099, 21172238), and the Found of Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences.

A bis(phosphine) (PCP) pincer palladium-catalyzed asymmetric alkylation of methylphenylphosphine with alkyl halides was developed for the synthesis of P-chiral phosphorus compounds in mild conditions. The corresponding products were obtained in high yields with moderate enantioselectivities. The possible catalytic cycle and stereochemical pathway have also been proposed via the Pincer-PdPMe(Ph) intermediate, which is generated from the reaction of Pd catalyst with methylphenylphosphine.

Key words: P-stereogenic compound, Pincer-Pd catalyst, methylphenylphosphine, asymmetric alkylation

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Li Chun, Li Weixun, Xu Sheng, Duan Weiliang. Pd-Catalyzed Asymmetric Alkylation of Methylphenylphosphine with Alkyl Halides for the Synthesis of P-stereogenic Compounds[J]. Chin. J. Org. Chem., 2013, 33(04): 799-802.

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钯催化甲基苯基膦氢的不对称烷基化反应合成含膦手性中心化合物

Pd-Catalyzed Asymmetric Alkylation of Methylphenylphosphine with Alkyl Halides for the Synthesis of P-stereogenic Compounds

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