ZnMe₂-Mediated, Direct Alkylation of Electron-Deficient N-Heteroarenes with 1,1-Diborylalkanes: Scope and Mechanism

Woohyun Jo, Seung-yeol Baek, Chiwon Hwang, Joon Heo, Mu-Hyun Baik* and Seung Hwan Cho*

*Korea Advanced Institute of Science and Technology, Daejeon, 34141; Pohang University of Science and Technology, Pohang, 37673, Republic of Korea, Email: mbaik2805kaist.ac.kr, seunghwanpostech.ac.kr

W. Jo, S.-y. Baek, C. Hwang, J. Heo, M.-H. Baik, S. H. Cho, J. Am. Chem. Soc., 2020, 142, 13235-13245.

DOI: 10.1021/jacs.0c06827

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Abstract

ZnMe₂ promotes a direct C2- or C4-selective primary and secondary alkylation of a broad range of pyridines and quinolines using 1,1-diborylalkanes as alkylation sources. While substituted pyridines and quinolines exclusively afford C2-alkylated products in good yields, simple pyridine delivers C4-alkylated pyridine with excellent regioselectivity.

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Key Words

quinolines

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ID: J48-Y2020