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2-炔基苯甲酸酯与芳基重氮盐的协同光氧化还原/金催化环化反应:3,4-二取代异香豆素的合成。

Cooperative photoredox/gold catalysed cyclization of 2-alkynylbenzoates with arenediazonium salts: synthesis of 3,4-disubstituted isocoumarins.

机构信息

Dipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica "A. Marchesini", Università degli Studi di Milano, Via Venezian, 21, 20133 Milano, Italy.

出版信息

Org Biomol Chem. 2022 Oct 26;20(41):8065-8070. doi: 10.1039/d2ob01371a.

DOI:10.1039/d2ob01371a
PMID:36200334
Abstract

Several isocoumarins have been synthesised in good to excellent yields starting from 2-alkynylbenzoates and arenediazonium salts. The strategy involves a domino arylation/oxo-cyclization catalysed by a dual photoredox/gold catalytic system. The reactions run under mild conditions at room temperature in wet acetonitrile under irradiation with a blue-LED lamp, in the presence of a cationic gold catalyst and a cheap organic photocatalyst. The scope is quite broad and allows the preparation of isocoumarins differently disubstituted in positions 3 and 4. A plausible reaction mechanism is proposed.

摘要

几种异香豆素已经通过从 2-炔基苯甲酸酯和芳基重氮盐出发以良好到优异的产率合成。该策略涉及双光氧化还原/金催化体系催化的串联芳基化/氧化环化。反应在温和条件下在室温下在潮湿的乙腈中进行,用蓝色 LED 灯照射,存在阳离子金催化剂和廉价的有机光催化剂。范围相当广泛,允许制备在 3 位和 4 位不同取代的异香豆素。提出了一种合理的反应机制。

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