铑（III）催化C-H活化微波辅助合成杂环：降冰片二烯为乙炔等价物

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-10 DOI:10.1021/acs.orglett.4c04334

Joyann S. Donaldson, Haojun Jiang, Dehuan Kong, Wei Li, Indrawan J. McAlpine, Sajiv K. Nair, Sylvie Sakata, Jillian E. Spangler, Nicole Sun, Michelle B. Tran-Dubé, Yang Zhou, Ryan L. Patman

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引用次数: 0

摘要

铑催化环化芳基/杂芳基o -戊酰羟肟酸和降冰片二烯的一般程序已经开发。采用降冰片二烯作为乙炔当量，可以利用各种杂环底物进行这种转化，这些底物在先前报道的条件下无法反应或经历竞争性的Lossen重排。与传统工艺相比，微波加热显著缩短了反应时间，并实现了一步处理。本文所述的条件已适用于克级合成，并应用于辉瑞临床候选药物的正式合成。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Microwave-Assisted Synthesis of Heterocycles via Rhodium(III)-Catalyzed C–H Activation: Norbornadiene as an Acetylene Equivalent

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Microwave-Assisted Synthesis of Heterocycles via Rhodium(III)-Catalyzed C–H Activation: Norbornadiene as an Acetylene Equivalent

General procedures for the rhodium-catalyzed annulation of aryl/heteroaryl O-pivaloyl hydroxamic acids and norbornadiene have been developed. Employing norbornadiene as an acetylene equivalent enables utilization of diverse heterocyclic substrates for this transformation which fail to react or undergo competitive Lossen rearrangement under previously reported conditions. Microwave heating significantly reduces reaction times compared to conventional protocols and allows a one-step process to be realized. The conditions described herein have been adapted for gram-scale synthesis and applied to the formal synthesis of Pfizer clinical candidates.

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来源期刊

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.