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布朗斯特酸催化的羰基-烯烃复分解反应:用磷钼酸作催化剂合成菲。

Brønsted Acid-Catalyzed Carbonyl-Olefin Metathesis: Synthesis of Phenanthrenes via Phosphomolybdic Acid as a Catalyst.

机构信息

School of Pharmacy & Bioengineering, Chongqing University of Technology, Chongqing 400054, China.

Chongqing Key Laboratory of Medicinal Chemistry & Molecular Pharmacology, Chongqing University of Technology, Chongqing 400054, China.

出版信息

J Org Chem. 2022 Jan 7;87(1):351-362. doi: 10.1021/acs.joc.1c02385. Epub 2021 Dec 20.

Abstract

Compared with the impressive achievements of catalytic carbonyl-olefin metathesis (CCOM) mediated by Lewis acid catalysts, exploration of the CCOM through Brønsted acid-catalyzed approaches remains quite challenging. Herein, we disclose a synthetic protocol for the construction of a valuable polycycle scaffold through the CCOM with the inexpensive, nontoxic phosphomolybdic acid as a catalyst. The current annulations could realize carbonyl-olefin, carbonyl-alcohol, and acetal-alcohol in situ CCOM reactions and feature mild reaction conditions, simple manipulation, and scalability, making this strategy a promising alternative to the Lewis acid-catalyzed COM reaction.

摘要

与路易斯酸催化的羰基-烯烃复分解反应(CCOM)令人印象深刻的成就相比,通过布朗斯台德酸催化方法探索 CCOM 仍然具有很大的挑战性。在此,我们披露了一种通过使用廉价、无毒的磷钼酸作为催化剂构建有价值的多环支架的合成方案。目前的环化反应可以实现羰基-烯烃、羰基-醇和缩醛-醇的原位 CCOM 反应,具有温和的反应条件、简单的操作和可扩展性,使得该策略成为路易斯酸催化 COM 反应的一种很有前途的替代方法。

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