STEREOSELECTIVE SYNTHESIS OF ALKENES AND ALKENYL SULFIDES FROM ALKENYL HALIDES USING PALLADIUM AND RUTHENIUM CATALYSTS
STEREOSELECTIVE SYNTHESIS OF ALKENES AND ALKENYL SULFIDES FROM ALKENYL HALIDES USING PALLADIUM AND RUTHENIUM CATALYSTS
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DOI：
10.1021/jo01328a016
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发表时间：
1979-01-01
影响因子：
3.6
通讯作者：
KONDO, K
中科院分区：
文献类型：
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作者：
MURAHASHI, SI;YAMAMURA, M;KONDO, K
在零价钯化合物存在下，烯基卤化物与有机锂化合物（例如烷基、芳基和杂环锂）反应，在化学计量和催化条件下立体选择性地形成烯烃。在相同的钯催化剂存在下，用硫醇根阴离子处理后，烯基卤化物也很容易立体选择性地转化为相应的烯基硫醚。这些反应在80℃下很容易发生，并且产率通常良好到优异。通过使用过渡金属克服了传统有机技术在sp2碳原子上进行亲核取代的困难。 1 通过卤代烯与格氏试剂或有机锂化合物交叉偶联形成碳-碳键是烯烃合成中有吸引力且重要的途径之一。通过卤代烯与有机基反应合成烯烃的化学计量方法
Alkenyl halides react with organolithium compounds, such as alkyl, aryl, and heterocyclic lithiums, in the presence of zerovalent palladium compounds to form alkenes stereoselectively under both stoichiometric and catalytic conditions. Alkenyl halides also are easily converted to the corresponding alkenyl sulfides stereoselectively upon treatment with thiolate anions in the presence of the same palladium catalyst. These reactions occur readily at 80 C and the yields are generally good to excellent.The difficulty of nucleophilic substitution at an sp2 carbon atom by conventional organic techniques is overcome by using transition metals. 1 Carbon-carbon bond formation by cross-coupling of alkenyl halides with either Grignard reagents or organolithium compounds is one of the attractive and important pathways for the synthesis of alkenes. Thestoichiometric process for synthesis of alkenes by the reaction of alkenyl halides with organo-