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
收藏
页码：544 / 551
页数：8
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