Ir(I)-catalyzed synthesis of N-substituted pyridones from 2-alkoxypyridines via C-O bond cleavage

Shiguang Pan; Naoto Ryu; Takanori Shibata

doi:10.1021/ol400557z

Ir(I)-catalyzed synthesis of N-substituted pyridones from 2-alkoxypyridines via C-O bond cleavage

Shiguang Pan, Naoto Ryu, Takanori Shibata^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

40 Citations (Scopus)

Abstract

A cationic Ir(I) complex-catalyzed O-to-N-alkyl migration in 2-alkoxypyridines bearing a secondary alkyl group on the oxygen atom by C-O bond cleavage is described. The present transformation gave various N-alkylpyridones in moderate to good yields. The addition of sodium acetate played a key role in suppressing β-hydrogen elimination.

Original language	English
Pages (from-to)	1902-1905
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	8
DOIs	https://doi.org/10.1021/ol400557z
Publication status	Published - 2013 Apr 19

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol400557z

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title = "Ir(I)-catalyzed synthesis of N-substituted pyridones from 2-alkoxypyridines via C-O bond cleavage",

abstract = "A cationic Ir(I) complex-catalyzed O-to-N-alkyl migration in 2-alkoxypyridines bearing a secondary alkyl group on the oxygen atom by C-O bond cleavage is described. The present transformation gave various N-alkylpyridones in moderate to good yields. The addition of sodium acetate played a key role in suppressing β-hydrogen elimination.",

author = "Shiguang Pan and Naoto Ryu and Takanori Shibata",

year = "2013",

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T1 - Ir(I)-catalyzed synthesis of N-substituted pyridones from 2-alkoxypyridines via C-O bond cleavage

AU - Pan, Shiguang

AU - Ryu, Naoto

AU - Shibata, Takanori

PY - 2013/4/19

Y1 - 2013/4/19

N2 - A cationic Ir(I) complex-catalyzed O-to-N-alkyl migration in 2-alkoxypyridines bearing a secondary alkyl group on the oxygen atom by C-O bond cleavage is described. The present transformation gave various N-alkylpyridones in moderate to good yields. The addition of sodium acetate played a key role in suppressing β-hydrogen elimination.

AB - A cationic Ir(I) complex-catalyzed O-to-N-alkyl migration in 2-alkoxypyridines bearing a secondary alkyl group on the oxygen atom by C-O bond cleavage is described. The present transformation gave various N-alkylpyridones in moderate to good yields. The addition of sodium acetate played a key role in suppressing β-hydrogen elimination.

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Ir(I)-catalyzed synthesis of N-substituted pyridones from 2-alkoxypyridines via C-O bond cleavage

Abstract

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