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KIM, Namhoon
분자활성 촉매반응 연구단
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C2-Selective C-H Methylation of Heterocyclic N-Oxides with Sulfonium Ylides

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Title
C2-Selective C-H Methylation of Heterocyclic N-Oxides with Sulfonium Ylides
Author(s)
Won An; Su Bin Choi; Namhoon Kim; Na Yean Kwon; Prithwish Ghosh; Sang Hoon Han; Neeraj Kumar Mishra; Sangil Han; Sungwoo Hong; In Su Kim
Subject
Crotonic Acid Derivative, ; Epoxidation, ; Dimethylsulfoxonium Methylide
Publication Date
2020-11-20
Journal
ORGANIC LETTERS, v.22, no.22, pp.9004 - 9009
Publisher
AMER CHEMICAL SOC
Abstract
A redox-neutral C2-selective methylation of heterocyclic N-oxides with sulfonium ylides is described herein. This report presents unprecedented findings for the utility of sulfonium ylides as the methylation source of N-heterocycles beyond the Corey-Chaykovsky reaction. Intriguingly, pyrrolidine plays a significant role in minimizing the reductive C2-methylation process. This method is characterized by its mild conditions, simplicity, and excellent site selectivity. The applicability of the developed protocol is showcased by the late-stage methylation and sequential transformations of complex drug molecules.
URI
https://pr.ibs.re.kr/handle/8788114/7534
DOI
10.1021/acs.orglett.0c03403
ISSN
1523-7060
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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