Double C—F Bond Activation through β-Fluorine Elimination: Nickel-Mediated [3+2] Cycloaddition of 2-Trifluoromethyl-1-alkenes with Alkynes

Tomohiro Ichitsuka; Takeshi Fujita; Tomohiro Arita

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Double C—F Bond Activation through β-Fluorine Elimination: Nickel-Mediated [3+2] Cycloaddition of 2-Trifluoromethyl-1-alkenes with Alkynes

机译：通过消除β-氟来实现双CF键活化：2-三氟甲基-1-烯烃与炔烃的镍介导的[3 + 2]环加成反应

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摘要

The nickel-mediated [3+2] cycloaddition of 2-trifluoromethyl-1-alkenes with alkynes afforded fluorine-containing multi-substituted cyclopentadienes in a regioselective manner. This reaction involves the consecutive two C-F bond cleavage of a trifluoromethyl or a pentafluoroethyl group through β-fluorine elimination.

机译：2-三氟甲基-1-烯烃与炔烃的镍介导的[3 + 2]环加成反应以区域选择性方式提供了含氟的多取代环戊二烯。该反应包括通过β-氟消除连续的两个三氟甲基或五氟乙基的C-F键裂解。

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《Angewandte Chemie》 |2014年第29期|共5页
作者
Tomohiro Ichitsuka; Takeshi Fujita; Tomohiro Arita;
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正文语种 eng
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关键词
alkynes; C—F bond activation; cycloaddition; cyclopentadienes; fluoroalkenes; nickel;

机译：炔烃;CF键活化;环加成;环戊二烯;氟代烯烃;镍;

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1. Double C—F Bond Activation through β-Fluorine Elimination: Nickel-Mediated [3+2] Cycloaddition of 2-Trifluoromethyl-1-alkenes with Alkynes [J] . Tomohiro Ichitsuka, Takeshi Fujita, Tomohiro Arita Angewandte Chemie . 2014,第29期

机译：通过消除β-氟来实现双CF键活化：2-三氟甲基-1-烯烃与炔烃的镍介导的[3 + 2]环加成反应
2. Theoretical Insight into C(sp3)–F Bond Activations and Origins of Chemo- and Regioselectivities of “Tunable” Nickel-Mediated/-Catalyzed Couplings of 2-Trifluoromethyl-1-alkenes with Alkynes [J] . Xiaomin Zhang, Yuxia Liu, Guang Chen, Organometallics . 2017,第19期

机译：对C（SP ^{3 ） - F键和区域选择性的“可调谐”镍介导/ - 催化的2-三氟甲基-1-烯烃与alkynes的粘合剂和地区的起源的理论洞察}
3. Pd-Catalyzed [3+2] cycloaddition of ketoimines with alkynes via directed sp~3 C-H bond activation [J] . Ying Xie, Tengfei Chen, Shaomin Fu, Chemical Communications . 2014,第73期

机译：通过直接的sp〜3 C-H键活化，钯催化酮亚胺与炔烃的[3 + 2]环加成反应
4. H Abstraction/O Rebound or 3+2 Cycloaddition: Dichotomy of C-H Bond Activation by Transition Metal Oxides [C] . G.Fu, W.S.Xia, Z.Guo, Asia-Pacific Congress on Catalysis . 2003

机译：H抽象/ o反弹或3 + 2环加成：过渡金属氧化物C-H键活化的二分法
5. Mechanistic investigation of copper(I) catalyzed azide-alkyne [3+2] cycloaddition [D] . Rodionov, Valentin O. 2007

机译：铜（I）催化叠氮化物-炔烃[3 + 2]环加成反应的机理研究
6. A Theoretical Study of the Relationship between the Electrophilicity ω Index and Hammett Constant σp in 3+2 Cycloaddition Reactions of Aryl Azide/Alkyne Derivatives [O] . Hicham Ben El Ayouchia, Hafid Anane, Moulay Lahcen El Idrissi Moubtassim, 2016

机译：芳基叠氮化物/炔烃衍生物的3 + 2环加成反应中亲电性ω指数与哈米特常数σp关系的理论研究
7. Cover Picture: Double CF Bond Activation through β-Fluorine Elimination: Nickel-Mediated 3+2 Cycloaddition of 2-Trifluoromethyl-1-alkenes with Alkynes (Angew. Chem. Int. Ed. 29/2014) [O] . Tomohiro Ichitsuka, Takeshi Fujita, Tomohiro Arita, 2014

机译：封面图片：通过β-氟消除双C 1F键活化：镍介导的3 + 2环加成2-三氟甲基-1-烯烃与alkynes（Angew.Chem.Int.29 / 2014）
8. Activation of Carbon-Fluorine Bonds by Oxidative Addition at Tungsten(0): An Electrochemical Study [R] . Russell, A., Osterberg, C., Blackwood, D., 1988

机译：通过在钨（0）上氧化加成来活化碳 - 氟键：电化学研究

Double C—F Bond Activation through β-Fluorine Elimination: Nickel-Mediated [3+2] Cycloaddition of 2-Trifluoromethyl-1-alkenes with Alkynes

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