Thermal [2+2]-cycloaddition between silylalkynes and allenylphenols followed by the nucleophilic addition of water: metal-free and economical synthesis of arylcyclobutenals

被引:6
|
作者
Ohno, Shohei [1 ]
Avena, Ramon Francisco [1 ]
Aoyama, Hiroshi [1 ]
Fujioka, Hiromichi [1 ]
Arisawa, Mitsuhiro [1 ]
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Yamada Oka 1-6, Suita, Osaka 5650871, Japan
关键词
ATOM ECONOMY; 2+2 CYCLOADDITION; ORGANIC-SYNTHESIS; STEP ECONOMY; ALLENYNES; POT; CONSTRUCTION; CYCLIZATIONS; CYCLOBUTANES; 1-NAPHTHOLS;
D O I
10.1039/c9gc04184b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, we report an unprecedented thermal [2 + 2]-cycloaddition between silylalkynes and allenylphenols to form an aromatizing cyclobutachromene intermediate, followed by the nucleophilic addition of water to yield functionalized arylcyclobutenals. This reaction is atom- and pot-economical because all the atoms contained in the starting material are retained in the final product, no other reactants are required, and it proceeds in one-pot.
引用
收藏
页码:1220 / 1228
页数:9
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