Metal-free C(sp3)-H bond sulfonyloxylation of 2-alkylpyridines and alkylnitrones

被引：8

作者：

Wang, Chang-Sheng ^{[1
]}

Dixneuf, Pierre H. ^{[1
]}

Soule, Jean-Francois ^{[1
]}

机构：

[1] Univ Rennes, CNRS, UMR6226, F-3500 Rennes, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 27期

关键词：

COPPER-CHELATING AZIDES; C-H FUNCTIONALIZATION; QUINOLINE N-OXIDES; ALPHA-TOSYLOXYLATION; RUTHENIUM COMPLEXES; KETONES; REARRANGEMENT; SULFONYLATION; DERIVATIVES; ANHYDRIDE;

D O I：

10.1039/c8ob01075g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyridin-2-ylmethyl tosylate derivatives are obtained in high yields from 2-alkylpyridine 1-oxides via a [3,3]-sigmatropic rearrangement of the adduct between 2-alkylpridine 1-oxides with benzenesulfonyl chlorides. Moreover, alkylnitrones also undergo [3,3]-sigmatropic rearrangement to give -tosylated ketones after hydrolysis. Substitution reactions with nucleophiles then lead to diverse useful functionalizations for the synthesis of pincer ligands.

引用

页码：4954 / 4957

页数：4

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