The Use of Calcium Carbide as Acetylene Source in a Three‐Component Coupling with ω‐Chlorinated Ketones and Primary Amines,Chemistry - A European Journal

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The Use of Calcium Carbide as Acetylene Source in a Three‐Component Coupling with ω‐Chlorinated Ketones and Primary Amines
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2018-10-17 , DOI: 10.1002/chem.201803669
Wim E. Van Beek ₁ , Karthik Gadde ₁ , Kourosch Abbaspour Tehrani ₁

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Calcium carbide was used in a Cu^I‐catalysed three‐component coupling with ω‐chlorinated ketones and primary amines to generate terminal 2‐alkynyl‐N‐heterocycles. The formation of an imine and the subsequent intramolecular substitution results in an active electrophilic iminium species, which can be alkynylated by in situ formed copper acetylide. A number of aliphatic primary (functionalised) amines and aliphatic or aromatic alkynes together with different alkyl‐ or aryl‐substituted γ‐ or δ‐chloroketones could be used. Simple acid–base workup instead of column chromatography can be applied to obtain the resulting 2‐alkynylpyrrolidines and 2‐alkynylpiperidines.

中文翻译：

碳化钙作为乙炔源在ω-氯化酮与伯胺三组分偶联中的应用

电石被用于Cu ^I催化的三组分与ω-氯代酮和伯胺的偶合中，生成末端2-炔基-N-杂环。亚胺的形成和随后的分子内取代产生活性的亲电亚胺，可以通过原位形成的乙炔铜进行炔化。可以使用许多脂族伯（官能化）胺和脂族或芳族炔烃，以及不同的烷基或芳基取代的γ-或δ-氯酮。简单的酸碱处理而不是柱色谱法可用于获得最终的2-炔基吡咯烷和2-炔基哌啶。

更新日期：2018-10-17

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