Palladium(0)-Catalyzed Cross-Coupling of Potassium (Z)-2-Chloroalk-1-enyl Trifluoroborates: A Chemo- and Stereoselective Access to (Z)-Chloroolefins and Trisubstituted Alkenes

Xavier Guinchard; Xavier Bugaut; Cyril Cook; Emmanuel Roulland

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Palladium(0)-Catalyzed Cross-Coupling of Potassium (Z)-2-Chloroalk-1-enyl Trifluoroborates: A Chemo- and Stereoselective Access to (Z)-Chloroolefins and Trisubstituted Alkenes

机译：钯（0）催化的（Z）-2-氯烷-1-烯基三氟硼酸钾的交叉偶联：对（Z）-氯烯烃和三取代的烯烃的化学和立体选择

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We describe the preparation of a series of new potassium trifluoroborates 1 and the study of their behaviour in a Pd0-catalyzed cross-coupling reaction. We found that compounds 1 are endowed with original properties as they behave as nucleophilic cross-coupling partners chemoselectively but also as ambivalent synthons. The usefulness of this methodology has been successfully illustrated by the first total synthesis of an N-acyl spermidine.

机译：我们描述了一系列新的三氟硼酸钾1的制备及其在Pd0催化的交叉偶联反应中的行为研究。我们发现化合物1具有独特的化学性质，因为它们具有化学选择性的亲核交叉偶联伴侣和矛盾的合成子。 N-酰基亚精胺的第一次全合成成功地说明了该方法的实用性。

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《Chemistry: A European journal》 |2009年第23期|共6页
作者
Xavier Guinchard; Xavier Bugaut; Cyril Cook; Emmanuel Roulland;
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正文语种 eng
中图分类应用化学;
关键词
alkenes; boron; crosscoupling; palladium; vinyl chloride;

机译：烯烃;硼;交叉偶联;钯;氯乙烯;

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1. Palladium(0)-Catalyzed Cross-Coupling of Potassium (Z)-2-Chloroalk-1-enyl Trifluoroborates: A Chemo- and Stereoselective Access to (Z)-Chloroolefins and Trisubstituted Alkenes [J] . Xavier Guinchard, Xavier Bugaut, Cyril Cook, Chemistry: A European journal . 2009,第23期

机译：钯（0）催化的（Z）-2-氯烷-1-烯基三氟硼酸钾的交叉偶联：对（Z）-氯烯烃和三取代的烯烃的化学和立体选择
2. Palladium-Catalyzed Cross-Coupling of Stereospecific Potassium Cyclopropyl Trifluoroborates with Aryl Bromides [J] . Guuo-Hua Fang, Zheng-Jun Yan, Min-Zhi Deng Organic letters . 2004,第3期

机译：立体催化环丙基三氟硼酸钾与芳基溴化物的钯催化交叉偶联
3. Palladium-Catalyzed Cross-Coupling of Stereospecific Potassium Cyclopropyl Trifluoroborates with Aryl Bromides [J] . Guuo-Hua Fang, Zheng-Jun Yan, Min-Zhi Deng Organic letters . 2004,第3期

机译：立体催化三氟硼酸钾环丙基钾与芳基溴化物的钯催化交叉偶联
4. Stereoselective Synthesis of Trisubstituted Alkenylboranes by Palladium-Catalyzed Reaction of Alkynyltriarylborates with Aryl Halides [C] . Naoki Ishida, Tatsuo Shinmoto, Tomoya Miura Symposium on Organometallic Chemistry . 2007

机译：钯催化反应与芳基卤化物的钯催化反应的立体选择性合成羟基芳基芳基硼酸盐的反应
5. Exploration of alpha-Diazocarbonyl Compounds for Transition-Metal Catalyzed Carbon-Carbon Bond Formations. Development of Palladium-Catalyzed Stereoselective Synthesis of Trisubstituted Alkenes and the Synthesis of Quaternary alpha,alpha-Heterodiaryl Carboxylic Acids by Rhodium-Catalyzed Multi-Component Coupling Reactions. [D] . Tsoi, Yuk Tai. 2012

机译：探索用于过渡金属催化的碳-碳键形成的α-重氮羰基化合物。铑催化的多组分偶合反应在钯催化的立体选择性合成三取代的烯烃上的发展和季铵的α，α-杂二芳基羧酸的合成。
6. Highly Regio- and Stereoselective Synthesis of (Z)-Trisubstituted Alkenes via Propyne Bromoboration and Tandem Pd-Catalyzed Cross-Coupling [O] . Chao Wang, Tomas Tobrman, Zhaoqing Xu, -1

机译：通过丙炔Bromoboration和串联钯催化的交叉偶联（Z）三取代烯烃的高度区域选择性和立体选择性合成
7. Stereoselective Synthesis of Trisubstituted Alkenes through Sequential Iron-Catalyzed Reductiveanti-Carbozincation of Terminal Alkynes and Base-Metal-Catalyzed Negishi Cross-Coupling [O] . Chi Wai Cheung, Xile Hu 2015

机译：通过序贯铁催化的烷基催化烯酮烷基酯的烷基溶液和基础金属催化的Negishi交叉耦合的立体选择性合成
8. Dispersion of Rh/Cu in a Sol-Gel Matrix. Highly Chemo- and Stereoselective Catalyst for the Reduction of Alkynes to Z-Alkenes. [R] . Tour, J. M., Pendalwar, S. L., Kafka, C. M., 1993

机译：溶胶 - 凝胶基质中Rh / Cu的分散。用于将炔烃还原为Z-烯烃的高度化学和立体选择性催化剂。

Palladium(0)-Catalyzed Cross-Coupling of Potassium (Z)-2-Chloroalk-1-enyl Trifluoroborates: A Chemo- and Stereoselective Access to (Z)-Chloroolefins and Trisubstituted Alkenes

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