Zirconium-Medicated Cross-Coupling of Terminal alkynes and Vinyl Bromides:Selectie synthesis of cyclobutene and 1,3-Diene Deriatives

Jose Barluenga; Felix Rodriguez; Lucia Alvarez-Rodrigo; Francisco J.Fananas

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Zirconium-Medicated Cross-Coupling of Terminal alkynes and Vinyl Bromides:Selectie synthesis of cyclobutene and 1,3-Diene Deriatives

机译：末端炔烃和乙烯基溴化物的锆药交叉偶联：环丁烯和1,3-二烯衍生物的选择性合成

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A diasteroselective synthesis of 1,3-butadiene or cyclobutene derivatives by a zirconium-mediated reaction of akenyllithium compounds and vinyl bromides is reported.The key steps involve the generation of zirconocene-alkyne complexes from haloalkenes and subsequent coupling with alkenyl bromides.Thus,formally the process supposes the cross-coupling reaction between a terminal alkyne and an alkenyl bromide.Moreover,th use of butyl vinyl ether instead of vinyl bromide as the unsaturated system allows an alterantive access to different 1,3-butadiene regioisomers.

机译：据报道，通过锆介导的烯基锂化合物和乙烯基溴化物的非对映选择性合成1,3-丁二烯或环丁烯衍生物。关键步骤涉及从卤代烯烃生成锆茂-炔烃配合物，然后与烯基溴化物偶合。该方法假定了末端炔烃和烯基溴化物之间的交叉偶联反应。此外，使用丁基乙烯基醚代替乙烯基溴化物作为不饱和体系可以交替获得不同的1,3-丁二烯区域异构体。

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《Chemistry: A European journal》 |2004年第1期|共8页
作者
Jose Barluenga; Felix Rodriguez; Lucia Alvarez-Rodrigo; Francisco J.Fananas;
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正文语种 eng
中图分类化学;
关键词
dienes; c-c coupling; cross-coupling; cyclobutenes; zirconium;

机译：二烯;c-c偶联;交叉偶联;环丁烯;锆;

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1. Zirconium-Medicated Cross-Coupling of Terminal alkynes and Vinyl Bromides:Selectie synthesis of cyclobutene and 1,3-Diene Deriatives [J] . Jose Barluenga, Felix Rodriguez, Lucia Alvarez-Rodrigo, Chemistry: A European journal . 2004,第1期

机译：末端炔烃和乙烯基溴化物的锆药交叉偶联：环丁烯和1,3-二烯衍生物的选择性合成
2. Copper(II) acetate/1,4-diphenyl-1,4-diazabuta-1,3-diene catalyzed Sonogashira cross-coupling of aryl halides with terminal alkynes under aerobic and solvent-free conditions [J] . Deng CL, Xie YX, Yin DL, Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2006,第20期

机译：乙酸铜（II）/ 1,4-二苯基-1,4-重氮杂丁-1,3-二烯在无氧和无溶剂条件下芳基卤化物与末端炔烃的Sonogashira交叉偶联
3. Stereoselective Synthesis of Trisubstituted (E,E)-1,3-Dienes by the Site-Selective Reductive Cross-Coupling of Internal Alkynes with TerminalAlkynes: A Fragment Coupling Reaction for Natural Product Synthesis [J] . Lark J. Perez, Heidi L. Shimp, Glenn C. Micalizio The Journal of Organic Chemistry . 2009,第19期

机译：内部炔烃与末端炔烃的位点选择性还原交叉偶联立体选择性合成三取代（E，E）-1,3-Dienes：天然产物合成的片段偶联反应
4. Nickel-Catalyzed Addition of C-H Bonds of Terminal Alkynes to 1,3-Dienes and Styrenes [C] . Masamichi Shirakura, Michinori Suginome Symposium on Organometallic Chemistry . 2008

机译：镍催化的添加末端炔烃的C-H键至1,3-二烯和苯乙烯
5. Synthesis of sterically-hindered 2,2-disubstituted ethyltrifluoroborate salts and their palladium-catalyzed cross-coupling with aryl and vinyl bromides. [D] . Guinn, Robert H. 2011

机译：位阻2,2-二取代的乙基三氟硼酸盐的合成及其钯与芳基和乙烯基溴的交叉偶联。
6. A Palladium-Catalyzed Three-Component Cross-Coupling of Conjugated Dienes or Terminal Alkenes with Vinyl Triflates and Boronic Acids [O] . Longyan Liao, Ranjan Jana, Kaveri Balan Urkalan, -1

机译：钯催化三组分共轭二烯或末端烯烃的交叉耦合与乙烯基三氟甲磺酸酯和硼酸类
7. Cyclobutene vs. 1,3-Diene Formation in the Gold-Catalyzed Reaction of Alkynes with Alkenes: The Complete Mechanistic Picture [O] . de Orbe, M.E., Amenós, L, Kirillova, M.S, 2017

机译：炔烃与烯烃的金催化反应中环丁烯与1,3-二烯的形成：完整的机理图
8. Bromide Ion Catalyzed Dimerization of 3,3-Diphenyl-6-oxa-3-silabicyclo3.1.0hexane. Structure Determination and Ring Contraction of 2,2,6,6-Tetraphenyl-4,8-divinyl-1,5-dioxa-2,6-disilacyclooctane and Synthesis of 2,24,4-Tetraphenyl-6-vinyl-1,3-dioxa-2,4-di [R] . Park, Y. T., Manuel, G., Bau, R., 1991

机译：溴化物离子催化3,3-二苯基-6-氧杂-3-硅杂双环-3.1己烷的二聚反应。 2,2,6,6-四苯基-4,8-二乙烯基-1,5-二氧杂-2,6-二硅杂环辛烷的结构测定和环收缩及2,24,4-四苯基-6-乙烯基-1的合成， 3-二氧杂-2,4-二

Zirconium-Medicated Cross-Coupling of Terminal alkynes and Vinyl Bromides:Selectie synthesis of cyclobutene and 1,3-Diene Deriatives

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