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三氟环己烯酯的三组分双官能化通过环己炔直接合成多功能环己烯
作者:小柯机器人 发布时间:2021/10/17 16:06:10

美国杜克大学Qiu Wang团队报道了三氟环己烯酯的三组分双官能化通过环己炔直接合成多功能环己烯。相关研究成果于2021年10月13日发表在《德国应用化学》。

应变环炔烃的双官能化为构建功能丰富的环炔烃的提供了一种简便、强大的策略。

该文中,研究人员公开了一种高效且灵活的方法来实现现成的三氟环己烯酯的碳卤代、二碳官能化、氨基卤代和氨基碳酸化。研究人员证明了锌酸盐碱/亲核体系在有效形成关键环己烯中间体和选择性添加各种碳和氮亲核剂方面的新用途。重要的是,利用得到的有机锌酸盐,可以结合广泛的亲电伙伴,以提供结构多样的环己烯基序。该方法的模块化以及即使是高度复杂的多环支架也可以一步轻松获得,证明该方法的重要性和实用性。

附:英文原文

Title: Three-Component Difunctionalization of Cyclohexenyl Triflates Direct Access to Versatile Cyclohexenes via Cyclohexynes

Author: Seoyoung Cho, E.J. McLaren, Qiu Wang

Issue&Volume: 2021-10-13

Abstract: Difunctionalization of strained cyclic alkynes presents a powerful strategy to build richly functionalized cyclic alkenes in an expedient fashion. Herein we disclose an efficient and flexible approach to achieve carbohalogenation, dicarbofunctionalization, aminohalogenation and aminocarbonation of readily available cyclohexenyl triflates. We have demonstrated the novel use of zincate base/nucleophile system for effective formation of key cyclohexyne intermediates and selective addition of various carbon and nitrogen nucleophiles. Importantly, leveraging the resulting organozincates enables the incorporation of a broad range of electrophilic partners to deliver structurally diverse cyclohexene motifs. The importance and utility of this method is also exemplified by the modularity of this approach and the ease in which even highly complex polycyclic scaffolds can be accessed in one step.

DOI: 10.1002/anie.202109482

Source: https://onlinelibrary.wiley.com/doi/10.1002/anie.202109482

期刊信息

Angewandte Chemie:《德国应用化学》,创刊于1887年。隶属于德国化学会,最新IF:12.959
官方网址:https://onlinelibrary.wiley.com/journal/15213773
投稿链接:https://www.editorialmanager.com/anie/default.aspx