Nucleophilic Ring Opening of Donor–Acceptor Cyclopropanes Catalyzed by a Brønsted Acid in Hexafluoroisopropanol,Organic Letters

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Nucleophilic Ring Opening of Donor–Acceptor Cyclopropanes Catalyzed by a Brønsted Acid in Hexafluoroisopropanol
Organic Letters ( IF 4.9 ) Pub Date : 2018-01-18 00:00:00 , DOI: 10.1021/acs.orglett.7b03688
Edward Richmond ₁ , Vuk D. Vuković ₁ , Joseph Moran ₁

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A general, Brønsted acid catalyzed method for the room temperature, nucleophilic ring opening of donor–acceptor cyclopropanes in fluorinated alcohol solvent, HFIP, is described. Salient features of this method include an expanded cyclopropane scope, including those bearing single keto-acceptor groups and those bearing electron-deficient aryl groups. Notably, the catalytic system proved amenable to a wide range of nucleophiles including arenes, indoles, azides, diketones, and alcohols.

中文翻译：

布朗斯台德酸在六氟异丙醇中催化的供体-受体环丙烷的亲核开环

描述了一种在室温下布朗斯台德酸催化的方法，该方法用于室温下供体-受体环丙烷在氟化醇溶剂HFIP中的亲核开环。该方法的显着特征包括扩大的环丙烷范围，包括带有单个酮基受体的环丙烷和带有电子缺陷的芳基的环丙烷。值得注意的是，催化体系证明适用于多种亲核试剂，包括芳烃，吲哚，叠氮化物，二酮和醇。

更新日期：2018-01-18

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