title: Transition-Metal-Free Regioselective Alkylation of Pyridine N-Oxides Using 1,1-Diborylalkanes as Alkylating Reagents.
abstract: Reported herein is an unprecedented base-promoted deborylative alkylation of pyridine N-oxides using 1,1-diborylalkanes as alkyl sources. The reaction proceeds efficiently for a wide range of pyridine N-oxides and 1,1-diborylalkanes with excellent regioselectivity. The utility of the developed method is demonstrated by the sequential C-H arylation and methylation of pyridine N-oxides. The reaction also can be applied for the direct introduction of a methyl group to 9-O-methylquinine N-oxide, thus it can serve as a powerful method for late-stage functionalization.
authors.affiliation: Department of Chemistry and Division of Advanced Nuclear Engineering, Pohang University of Science and Technology (POSTECH), Pohang, 790-784, Rep. of Korea.
authors.forename: Woohyun
authors.initials: W
authors.lastname: Jo
authors.affiliation: Department of Chemistry and Division of Advanced Nuclear Engineering, Pohang University of Science and Technology (POSTECH), Pohang, 790-784, Rep. of Korea.
authors.forename: Junghoon
authors.initials: J
authors.lastname: Kim
authors.affiliation: Department of Chemistry and Division of Advanced Nuclear Engineering, Pohang University of Science and Technology (POSTECH), Pohang, 790-784, Rep. of Korea.
authors.forename: Seoyoung
authors.initials: S
authors.lastname: Choi
authors.affiliation: Department of Chemistry and Division of Advanced Nuclear Engineering, Pohang University of Science and Technology (POSTECH), Pohang, 790-784, Rep. of Korea. seunghwan@postech.ac.kr.
authors.forename: Seung Hwan
authors.initials: SH
authors.lastname: Cho
keywords: alkylation; boron; heterocycles; regioselectivity; transition-metal-free synthesis