Palladium-Catalyzed Bicycloaromatization of o-(Alkynyl)styrenes with Alkynes: Economical Access to Chrysene Derivatives

IF 4.9 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-09-30 DOI:10.1021/acs.orglett.4c03056
Bing Liu, Sen Lei, Zhendong Cheng, Liwei Zhou, Guobo Deng, Yun Liang, Yuan Yang
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Abstract

Herein, a palladium-catalyzed bicycloaromatization of o-(alkynyl)styrenes with alkynes is reported. In this protocol, the 6-endo-dig cyclization of o-(alkynyl)styrenes is followed by deprotonation to complete the first cycloaromatization, and then, a regioselective alkyne insertion/C–H activation occurs to achieve the second cycloaromatization, resulting in atom- and step-economical syntheses of polysubstituted chrysenes. Notably, the products can be further used to construct π-extended arenes using the Scholl reaction.

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钯催化邻(炔基)苯乙烯与炔烃的双环芳构化:经济地获得菊烯衍生物
本文报告了一种钯催化的邻(炔基)苯乙烯与炔烃的双环芳香化反应。在该方案中,邻(炔基)苯乙烯的 6-内向-歧化环化之后进行去质子化以完成第一次环芳烃化,然后进行区域选择性炔插入/C-H 活化以实现第二次环芳烃化,从而以原子和步骤经济的方式合成多取代的菊烯。值得注意的是,这些产物可进一步用于利用 Scholl 反应构建 π-扩展的炔烃。
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来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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