RETRACTED: Direct synthesis of 1-naphthylamines enabled by 6-endo-dig cyclization strategy using copper catalysis (Retracted Article)

被引：1

作者：

Ma, Peng ^{[1
]}

Wang, Jianhui ^{[1
]}

Liu, Guiyan ^{[2
]}

机构：

[1] Tianjin Univ, Coll Sci, Dept Chem, Tianjin 300350, Peoples R China

[2] Tianjin Normal Univ, Coll Chem, Tianjin Key Lab Struct & Performance Funct Mol Ti, Tianjin 300387, Peoples R China

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2022年 / 36卷 / 06期

基金：

中国国家自然科学基金;

关键词：

1-naphthylamine derivatives; 6-endo-dig cyclization; copper catalysis; decarboxylative amination; halide exchange; C-H ACTIVATION; ARYL CHLORIDES; AMINATION; KETONES; AMINOBENZANNULATION; COUPLINGS; FUNCTIONALIZATION; AROMATIZATION; MONOARYLATION; CONSTRUCTION;

D O I：

10.1002/aoc.6679

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Here, we describe a facile approach for the synthesis of substituted 1-naphthylamines via three-component 6-endo-dig cyclization of terminal alkynes with 2-bromoaryl ketones, primary or secondary amines in water under Pd-free conditions. The Cu(I) catalytic system avoids a fundamental problem related to these substrates, which competitively evolve through 5-endo-dig cyclization pathways under metal catalysis. This unique performance unlocks a rapid access to a diverse 1-naphthylamines library that previously required longer synthetic routes. The synthetic potential of this method was further demonstrated by the gram-scale synthesis, and the mechanism study showed that the reaction experienced sequential halide exchange, imine-enamine tautomerization and 6-endo-dig cyclization.

引用

页数：8