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Transition‐Metal‐Free Regioselective Alkylation of Pyridine N ‐Oxides Using 1,1‐Diborylalkanes as Alkylating Reagents
Author(s) -
Jo Woohyun,
Kim Junghoon,
Choi Seoyoung,
Cho Seung Hwan
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201603329
Subject(s) - regioselectivity , alkylation , pyridine , reagent , chemistry , alkyl , transition metal , combinatorial chemistry , metal , methylation , organic chemistry , medicinal chemistry , catalysis , biochemistry , gene
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.