Catalytic Cycloisomerization of Enyne Diesters Derived from Biaryls and Related Substrates
作者:Manoj K. Saini、Karmdeo Prajapati、Rashi Sharma、Ashok K. Basak
DOI:10.1002/adsc.202300225
日期:2023.7.4
Enyne diesters derived from biaryls and related substrates undergo intramolecular [2+2]-cycloaddition and concomitant cyclo-reversion when treated with 10 mol% In(OTf)3 in 1,2-dichloroethane. This enyne metathesis type cycloisomerization reaction enables the synthesis of phenanthrene, benzophenanthrene, benzotetraphene and other polycyclic (hetero)aromatic compounds bearing a synthetically useful diethyl
当用 10 mol% In(OTf) 3 的1,2-二氯乙烷溶液处理时,衍生自联芳基和相关底物的烯炔二酯会发生分子内 [2+2]-环加成和伴随的环化逆转。这种烯炔复分解型环异构化反应能够以步骤和原子经济的方式合成菲、苯并菲、苯并四吩和其他带有合成有用的β-(杂)亚芳基丙二酸二乙酯部分的多环(杂)芳香族化合物。In(OTf) 3 -在底物5a和5b上催化两个独立的分子内环异构化,可直接生成苯并四吩6a和6b含有双(β-苯基亚甲基丙二酸二乙酯)部分。被两个不同芳族基团取代的四取代亚乙烯基丙二酸酯4a通过Pd催化的立体选择性脱羧芳基化反应立体选择性转化为含全碳四取代烯烃的三芳基E-和Z-异构体( 8a、8a'和8b ) 。