Metal-Free Radical-Mediated C(sp3)-H Heteroarylation of Alkanes

Xin Shao; Xinxin Wu; Shuo Wu; Chen Zhu

doi:10.1021/acs.orglett.0c02475

Metal-Free Radical-Mediated C(sp³)-H Heteroarylation of Alkanes

Org Lett. 2020 Oct 2;22(19):7450-7454. doi: 10.1021/acs.orglett.0c02475. Epub 2020 Sep 24.

Authors

Xin Shao¹, Xinxin Wu¹, Shuo Wu¹, Chen Zhu^{1

2}

Affiliations

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China.
² Key Laboratory of Synthesis Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032, China.

PMID: 32969219
DOI: 10.1021/acs.orglett.0c02475

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.