Hydrogen-Transfer-Mediated Direct β-Alkylation of Aryl-1,8-naphthyridines with Alcohols under Transition Metal Catalyst Free Conditions

Organic Letters
Biao XiongMin Zhang

Abstract

By employing abundant and sustainable alcohols as the alkylating reagents, a new and direct alkylation method has been demonstrated. This method enables the selective alkylation of the less substituted pyridyl ring at the β-site of aryl-1,8-naphthyridines, affording the desired products in moderate to excellent yields upon isolation. The method proceeds under transition-metal-free conditions in an atom- and step-economic fashion and liberates water as the sole byproduct. Mechanistic investigations suggest the reaction undergoes a hydrogen-transfer-mediated alkylation mode.

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Jun 9, 2016·Chemistry : a European Journal·Dhruba Sarkar, Vladimir Gevorgyan
Aug 15, 2018·Angewandte Chemie·Gwilherm Evano, Cédric Theunissen
Jul 31, 2019·Organic & Biomolecular Chemistry·Shaohua JiangXiuwen Chen

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