Reactions of Donor–Acceptor Cyclopropanes with Naphthoquinones: Redox and Lewis Acid Catalysis Working in Concert,Angewandte Chemie International Edition

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Reactions of Donor–Acceptor Cyclopropanes with Naphthoquinones: Redox and Lewis Acid Catalysis Working in Concert
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2017-07-19 07:51:06 , DOI: 10.1002/anie.201703732
Alexander Lücht ₁ , Lukas J. Patalag ₁ , André U. Augustin ₁ , Peter G. Jones ₂ , Daniel B. Werz ₁

Affiliation

Reactions of 2-arylcyclopropane dicarboxylates with naphthoquinones are reported. The key feature was the use of catalytic amounts of SnCl₂, which acts as both an electron donor and a Lewis acid. By an in situ umpolung of naphthoquinone the formerly electrophilic species is converted into a nucleophile that is able to trigger the ring-opening of the three-membered ring with formation of a new C−C bond. Treatment of these products with base under oxidative conditions resulted—through loss of methyl formate—in cyclopentannulated products with fully conjugated π systems exhibiting intensive absorptions in the visible range.

中文翻译：

供体-受体环丙烷与萘醌的反应：氧化还原和路易斯酸催化协同作用

报道了2-芳基环丙烷二羧酸酯与萘醌的反应。关键特征是使用催化量的SnCl ₂，它既充当电子给体，又充当路易斯酸。通过原位萘醌的聚醚酮，以前的亲电物质被转化为亲核试剂，该亲核试剂能够触发三元环的开环并形成新的C-C键。这些产物在氧化条件下用碱处理，是由于甲酸甲酯的损失，导致了在完全可见光范围内具有强吸收作用的完全共轭π系统的环戊烯化产品。

更新日期：2017-07-20

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