Ru-catalyzed activation of sp3 C-O bonds: O- to N-alkyl migratory rearrangement in pyridines and related heterocycles

被引：79

作者：

Yeung, Charles S. ^{[1
]}

Hsieh, Tom H. H. ^{[1
]}

Dong, Vy M. ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

CHEMICAL SCIENCE | 2011年 / 2卷 / 03期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

CROSS-COUPLING REACTION; H BOND; EFFICIENT SYNTHESIS; ALLYLIC ETHERS; ARYL TOSYLATES; NITROGEN ATOM; PALLADIUM; FUNCTIONALIZATION; ARYLATION; ACID;

D O I：

10.1039/c0sc00498g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a novel strategy for the formal activation of sp(3) C-O bonds under Ru catalysis. In this reaction, an O-alkylpyridine undergoes migratory rearrangement to its corresponding N-alkylpyridone via coordination of the Lewis basic N atom. This transformation represents the first general catalytic approach to O- to N-alkyl migration in N-containing heterocycles. Extension of this methodology to other heterocycles, including O-alkylpyridazines and O-alkylazoles, was achieved.

引用

页码：544 / 551

页数：8

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