Heteroaromatic Tosylates as Electrophiles in Regioselective Mizoroki-Heck-Coupling Reactions with Electron-Rich Olefins

Gogsig TM; Lindhardt AT; Dekhane M; Grouleff J; Skrydstrup T

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Heteroaromatic Tosylates as Electrophiles in Regioselective Mizoroki-Heck-Coupling Reactions with Electron-Rich Olefins

机译：杂芳族甲苯磺酸盐作为亲电子与富电子烯烃的区域选择性咪唑罗基-Heck偶联反应中的亲电子体

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摘要

Heteroaromatic 2-pyridyl tosylates were successfully applied as electrophiles in palladium(0)-catalyzed Mizoroki-Heck-coupling reactions to electron-rich olefins with complete alpha-regioselectivity. This protocol represents a general strategy for the application of pyridyl tosylates and mesylates in the Mizoroki-Heck coupling. The catalytic system also proved adaptable to changes in the heteroaromatic core as well as large-scale applications. Finally, the synthetic utility of the functionalized alpha-heteroarylvinyl amides was established providing straightforward access to highly functionalized heteroaromatic compounds including chiral benzylic amide derivatives.

机译：杂芳族2-吡啶基甲苯磺酸盐已成功地用作亲电试剂，在钯（0）催化的Mizoroki-Heck偶联反应中，具有完全的α-区域选择性的富电子烯烃。该协议代表在Mizoroki-Heck偶联中应用吡啶基甲苯磺酸盐和甲磺酸盐的一般策略。该催化系统还证明可适应杂芳族核的变化以及大规模应用。最后，建立了官能化的α-杂芳基乙烯基酰胺的合成实用程序，可以直接获得包括手性苄基酰胺衍生物在内的高度官能化的杂芳族化合物。

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《Chemistry: A European journal》 |2009年第24期|共6页
作者
Gogsig TM; Lindhardt AT; Dekhane M; Grouleff J; Skrydstrup T;
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正文语种 eng
中图分类应用化学;
关键词
aryl tosylates; C-C coupling; Mizoroki–Heck coupling; heterocycles; palladium;

机译：甲苯磺酸芳基酯;C-C偶联;Mizoroki-Heck偶联;杂环;钯;

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专利

1. Heteroaromatic Tosylates as Electrophiles in Regioselective Mizoroki-Heck-Coupling Reactions with Electron-Rich Olefins [J] . Gogsig TM, Lindhardt AT, Dekhane M, Chemistry: A European journal . 2009,第24期

机译：杂芳族甲苯磺酸盐作为亲电子与富电子烯烃的区域选择性咪唑罗基-Heck偶联反应中的亲电子体
2. Regioselective Heck Couplings of α,β-Unsaturated Tosylates and Mesylates with Electron-Rich Olefins [J] . Anders Lindhardt Hansen, Troels Skrydstrup Organic letters . 2005,第25期

机译：α，β-不饱和甲苯磺酸盐和甲磺酸盐与富电子烯烃的区域选择性Heck偶联
3. Regioselective Heck Couplings of alpha,beta-Unsaturated Tosylates and Mesylates with Electron-Rich Olefins [J] . Anders Lindhardt Hansen, Troels Skrydstrup Organic letters . 2005,第25期

机译：α，β-不饱和甲苯磺酸盐和甲磺酸盐与富含电子的烯烃的区域选择性Heck偶联
4. 2-Iodoimidazolium salt-catalyzed 4+2 cycloaddition reaction ofimines and electron-rich olefins [C] . Takumi Suzuki, Satoru Kuwano, Takayoshi Arai 日本化学会春季年会 . 2020

机译：2-碘咪唑盐催化4 + 2环加成反应咪木和电子富含烯烃
5. Exploration of the inverse-electron-demand Diels-Alder (IEDDA) reaction. Rapid access to benzocoumarins via IEDDA-driven domino reactions of coumarin-fused electron-deficient dienes with electron-rich dienophiles. [D] . Pottie, Ian R. 2003

机译：逆电子需求Diels-Alder（IEDDA）反应的探索。通过IEDDA驱动的香豆素融合的电子缺陷二烯与富电子的亲二烯体的多米诺反应，可快速获得苯并香豆素。
6. Nickel-Catalyzed Carbonyl-Ene-Type Reactions: Selective for Alpha Olefins and More Efficient with Electron-Rich Aldehydes [O] . Chun-Yu Ho, Sze-Sze Ng, Timothy F. Jamison -1

机译：镍催化的羰基-烯类反应：对α烯烃具有选择性并且对富含电子的醛更有效
7. Regioselective Heck Couplings of a, b-Unsaturated Tosylates and Mesylates with Electron-Rich Olefins [O] . -1

机译：具有电子富含电子烯烃的A，B-不饱和甲磺酸盐和甲磺酸盐的区域选择性的偶联

Heteroaromatic Tosylates as Electrophiles in Regioselective Mizoroki-Heck-Coupling Reactions with Electron-Rich Olefins

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