Carbolithiation of Chloro-Substituted Alkynes: A New Access to Vinyl Carbenoids

Rudy Lhermet; Maha Ahmad; Catherine Fressigné; Bernard Silvi; Muriel Durandetti; Jacques Maddaluno

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Carbolithiation of Chloro-Substituted Alkynes: A New Access to Vinyl Carbenoids

机译：氯代炔烃的碳环化：乙烯基类胡萝卜素的新途径。

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摘要

The intramolecular carbolithiation of a series of chloro-substituted alkynes leads to exocyclic alkylidene carbenoids of which both nucleophilic and electrophilic characters can be drove. A sole stereoselective 5-exo-dig addition takes place, probably because of a strong and persisting Li–Cl interaction arising before the transition state.

机译：一系列氯取代的炔烃的分子内碳甲酸酯化导致环外亚烷基类胡萝卜素，其亲核和亲电特性均可被驱动。发生唯一的立体选择性5-exo-dig加成反应，可能是由于在过渡态之前出现了强而持久的Li-Cl相互作用。

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《Chemistry: A European journal》 |2014年第33期|共6页
作者
Rudy Lhermet; Maha Ahmad; Catherine Fressigné; Bernard Silvi; Muriel Durandetti; Jacques Maddaluno;
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正文语种 eng
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关键词
intramolecular; carbolithiation; series;

机译：分子内;碳化合成;系列;

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专利

1. Carbolithiation of Chloro-Substituted Alkynes: A New Access to Vinyl Carbenoids [J] . Rudy Lhermet, Maha Ahmad, Catherine Fressigné, Chemistry: A European journal . 2014,第33期

机译：氯代炔烃的碳环化：乙烯基类胡萝卜素的新途径。
2. A stereospecific access to allyic systems using rhodium(II)-vinyl carbenoid insertion into Si-H, O-H, and N-H bonds [J] . Priyadarshanie Bulugahapitiya, Yannick Landais, Liliana Parra-Rapado The Journal of Organic Chemistry . 1997,第6期

机译：使用铑（II）-乙烯基类胡萝卜素插入Si-H，O-H和N-H键的立体定向进入烯丙基体系
3. Ruthenium-Catalyzed Intermolecular Coupling of Vinylic 1,2- Bisboronates with Alkynes: Stereoselective Access to Boryl- Substituted Homoallylic Alcohols [J] . Barry M. Trost, Guoting Zhang Journal of the American Chemical Society . 2020,第16期

机译：钌催化的乙烯1,2-双硼酸酯与炔烃的分子间偶联：立体选择性地获得硼烷基取代的均烷醇
4. Microwave-assisted Synthesis of Anilinocarbonyl Acetylene: A Quick Access to Terminal Alkynes [C] . Yubo Jiang, Chunmei Han, Xueqiu Liang International Forum on Materials Analysis and Testing Technology . 2014

机译：微波辅助合成苯胺羰基乙炔：快速进入终端炔烃
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6. Fritsch–Buttenberg–Wiechell rearrangement of magnesium alkylidene carbenoids leading to the formation of alkynes [O] . Tsutomu Kimura, Koto Sekiguchi, Akane Ando, 2021

机译：Fritch-buttenberg-wiechell重新排列亚烷基羧酸镁导致alkynes的形成
7. Stereoselective Access to Highly Substituted Vinyl Ethers via Trans-Difunctionalization of Alkynes with Alcohols and Iodine(III) Electrophile [O] . Wei Ding, Jinkui Chai, Junliang Wu, 2020

机译：通过醇酸和碘（III）亲电子通过炔烃的逆二官能化对高度取代的乙烯基醚的立体选择性进入

Carbolithiation of Chloro-Substituted Alkynes: A New Access to Vinyl Carbenoids

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