Catalytic Formal [4+2] Cycloadditions between Unactivated Allenes and N-Hydroxyaniline Catalyzed by AuCl3/CuCl2/O2

被引：29

作者：

Chen, Jian-Ming ^{[1
]}

Chang, Chin-Jung ^{[1
]}

Ke, Yao-Jin ^{[1
]}

Liu, Rai-Shung ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 10期

关键词：

DIELS-ALDER REACTIONS; GOLD CATALYSIS; AEROBIC OXIDATION; ENANTIOSELECTIVE SYNTHESIS; NITROSO-COMPOUNDS; HYDROXAMIC ACIDS; RELAY CATALYSIS; ENE REACTION; HYDROXYLAMINES; DERIVATIVES;

D O I：

10.1021/jo500009x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

AuCl3-catalyzed formal [4 + 2]-cycloadditions between substituted allenes and N-hydroxyanilines are described. This reaction sequence comprises initial isomerizations of allenes to butadienes under N-2 and subsequent oxidations of N-hydroxyanilines to nitrosoarenes under O-2. CuCl2 (5 mol %) was added in the second step to increase the oxidation efficiency. The reactions are compatible with various 1,1-di- and 1,1,3-trisubstituted allenes and N-hydroxyaniline derivatives. Our experimental data reveal that the roles of AuCl3 are 3-fold, including catalytic oxidations of N-hydroxyaniline derivatives to nitrosoarenes, isomerizations of alkyl-substituted allenes to dienes, and final nitroso/butadiene [4 + 2] cycloadditions.

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页码：4306 / 4311

页数：6

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