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Metal-Free Radical-Mediated C(sp<sup>3</sup>)–H Heteroarylation of Alkanes

Xin Shao, Xinxin Wu, Shuo Wu, Chen Zhu

2020Organic Letters71 citationsDOI

Abstract

Herein we disclose a metal-free, N/O-centered radical-promoted Minisci reaction, in which the coupling of various heteroarenes with simple alkanes proceeds under mild conditions. The reaction conditions are neutral; no extra acid is added to preactivate N-heteroarenes in the Minisci reaction. The N-/O-centered radicals are generated directly from amide (TsNHMe) or alcohol (CF3CH2OH) under visible-light irradiation. This green and eco-friendly synthetic process may find potential use in medicinal chemistry.

Topics & Concepts

ChemistryRadicalAmideMetalAlcoholCoupling reactionPhotochemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
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