Nucleophilic Aromatic Substitution (SNAr) as an Approach to Challenging Carbohydrate-Aryl Ethers

被引：64

作者：

Henderson, Alexander S. ^{[1
]}

Medina, Sandra ^{[1
]}

Bower, John F. ^{[1
]}

Galan, M. Carmen ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 19期

基金：

英国工程与自然科学研究理事会;

关键词：

CATALYTIC ENANTIOSELECTIVE CYANOSILYLATION; ALKYL-ARYL; BOND FORMATION; CHEMISTRY; ALCOHOLS; HALIDES;

D O I：

10.1021/acs.orglett.5b02413

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and practical route to carbohydrate aryl ethers by nucleophilic aromatic substitution (SNAr) is reported. Upon treatment with KHMDS, C-O bond formation occurs between carbohydrate alcohols and a diverse range of fluorinated (hetero)aromatics to provide the targets in good to excellent yields. Commercially available arylating agents, high atom economy, and high regioselectivity are notable features of the protocol. The aryl ether products have potential for wide-ranging applications as exemplified by the synthesis of a novel chiral P,N-ligand.

引用

页码：4846 / 4849

页数：4

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