Gold-Catalyzed Addition of N-Hydroxy Heterocycles to Alkynes and Subsequent 3,3-Sigmatropic Rearrangement

被引：36

作者：

Kumar, Manish ^{[1
]}

Scobie, Martin ^{[2
]}

Mashuta, Mark S. ^{[1
]}

Hammond, Gerald B. ^{[1
]}

Xu, Bo ^{[1
]}

机构：

[1] Univ Louisville, Dept Chem, Louisville, KY 40292 USA

[2] Karolinska Inst, Dept Med Biochem & Biophys, Sci Life Lab, Div Translat Med & Chem Biol, Stockholm, Sweden

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 04期

基金：

美国国家科学基金会;

关键词：

REGIOSELECTIVE OXIDATION; C-C; KETONES; BONDS; CARBENOIDS; SULFOXIDES; MECHANISM; ALCOHOLS; INDOLES;

D O I：

10.1021/ol4000789

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Gold-catalyzed intermolecular addition of hydroxybenzotriazole derivatives to alkynes at room temperature, gives vinyl ethers 3 in high yields and with excellent regioselectivity. Unlike many other vinyl ethers, 3 can easily be purified by regular silica-gel chromatography. On heating, 3,3-sigmatropic rearrangement of 3 gives access to highly functionalized benzotriazoles. This two-step sequence represents an efficient oxygen transfer protocol which incorporates a nucleophilic oxygen atom Into an alkyne group. Reaction of 3 with an electrophilic fluorinating reagent (Selectfluor) gives a fluorinated ketone regioselectively and in high yield.

引用

页码：724 / 727

页数：4

共 35 条

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