Trifluoromethylation-Initiated Remote Cross-Coupling of Carbonyl Compounds to Form Carbon-Heteroatom/Carbon Bonds

Huang Lin; Zheng Sheng-Cai; Tan Bin; Liu Xin-Yuan

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Trifluoromethylation-Initiated Remote Cross-Coupling of Carbonyl Compounds to Form Carbon-Heteroatom/Carbon Bonds

机译：三氟甲基化引发的羰基化合物的远程交叉偶联形成碳-杂原子/碳键

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摘要

By involving the reversal of conventional reactivity expectations without external oxidants, we describe a novel and convenient protocol of remote cross-coupling of carbonyl compounds with a series of common and simple nucleophiles. This cross-coupling is triggered by radical trifluoromethylation of alkenes, thereby achieving highly selective remote difunctionalization of alkenes and alpha-position of the carbonyl group for facile access to trifluoromethyl alpha-halo- and alpha-cyanocarbonyl compounds. The reaction exhibits a broad substrate scope with excellent functionality tolerance and many different types of nucleophiles; further synthetic applicability of the obtained compounds proved to be suitable, thus showing great potential for synthetic utility.

机译：通过涉及无需外部氧化剂即可逆转常规反应活性的预期，我们描述了一种新颖便捷的方案，可将羰基化合物与一系列常见和简单的亲核试剂进行远程交叉偶联。烯烃的自由基三氟甲基化触发了这种交叉偶联，从而实现了烯烃的高度选择性远程双官能化和羰基的α-位置，从而可轻松获得三氟甲基α-卤代和α-氰基羰基化合物。该反应具有广泛的底物范围，具有出色的功能耐受性和许多不同类型的亲核试剂。所获得的化合物的进一步的合成适用性被证明是合适的，因此显示出巨大的合成应用潜力。

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《Chemistry: A European journal》 |2015年第18期|共5页
作者
Huang Lin; Zheng Sheng-Cai; Tan Bin; Liu Xin-Yuan;
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1; 5-H radical shift; alkenes; C-H functionalization; cross-coupling; trifluoromethylation;

机译：1;5-H自由基转移;烯烃;C-H官能化;交叉偶联;三氟甲基化;

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1. Trifluoromethylation-Initiated Remote Cross-Coupling of Carbonyl Compounds to Form Carbon-Heteroatom/Carbon Bonds [J] . Huang Lin, Zheng Sheng-Cai, Tan Bin, Chemistry: A European journal . 2015,第18期

机译：三氟甲基化引发的羰基化合物的远程交叉偶联形成碳-杂原子/碳键
2. Transition Metal-Catalyzed Cross-Coupling and the Heck Coupling Processes:Powerful Reactions for Carbon-Carbon and Carbon-Heteroatom Bond Formation [J] . Stephen L.Buchwald Advanced synthesis & catalysis . 2004,第13a15期

机译：过渡金属催化的交叉偶联和Heck偶联过程：碳-碳和碳-杂原子键形成的强大反应
3. Carbon-carbon and carbon-heteroatom bond formation on solid phase using cationic iron carbonyl complexes [J] . Graden H, Olsson T, Kann N Organic letters . 2005,第16期

机译：使用阳离子羰基铁络合物在固相上形成碳-碳和碳-杂原子键
4. C-C Bond Formation of Carbonyl Compounds Catalyzed by a Mononuclear Copper(II)-Superoxide Complex [C] . Tsukasa Abe, Yuma Morimoto, Hideki Sugimoto 日本化学会春季年会講演予稿集 . 2018

机译：由单核铜（II）催化的羰基化合物的C-C键形成 - 氧化物复合物
5. Chelation-assisted palladium-catalyzed activation of C-H bonds: A new avenue for carbon-heteroatom and carbon-carbon bond formation. [D] . Giri, Ramesh. 2009

机译：螯合辅助的钯催化的C-H键活化：形成碳-杂原子和碳-碳键的新途径。
6. Recent advances in the synthetic and mechanistic aspects of the ruthenium-catalyzed carbon-heteroatom bond forming reactions of alkenes and alkynes [O] . Chae S. Yi -1

机译：钌催化的碳 - 杂原子键形成反应的合成和机械方面的最新进展和炔烃
7. Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with vinyl triflates β-substituted by a carbonyl group: efficient synthesis of β-boryl-α,β-unsaturated carbonyl compounds and their synthetic utility [O] . Ishiyama, Tatsuo, Takagi, Jun, Kamon, Akihiro, 2003

机译：双（频哪醇）二硼与钯被羰基取代的乙烯基三氟甲磺酸酯的钯催化交叉偶联反应：β-硼基-α，β-不饱和羰基化合物的有效合成及其合成应用

Trifluoromethylation-Initiated Remote Cross-Coupling of Carbonyl Compounds to Form Carbon-Heteroatom/Carbon Bonds

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