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

被引：4

作者：

Pirovano, Valentina ^{[1
]}

Brambilla, Elisa ^{[1
]}

Fanciullacci, Giorgia ^{[1
]}

Abbiati, Giorgio ^{[1
]}

机构：

[1] Univ Milan, Dipartimento Sci Farmaceut, Sez Chim Gen & Organ A Marchesini, Via Venezian 21, I-20133 Milan, Italy

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 41期

关键词：

VISIBLE-LIGHT PHOTOREDOX; ARYLDIAZONIUM SALTS; ALPHA-PYRONES; BENZOIC-ACIDS; EOSIN Y; ANNULATION; DERIVATIVES; ALKYNES; ESTERS;

D O I：

10.1039/d2ob01371a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

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收藏

页码：8065 / 8070

页数：6

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