Practical synthesis of isocoumarins via Rh(III)-catalyzed C-H activation/annulation cascade

被引：6

作者：

Gao, Qian-Ci ^{[1
,2
]}

Li, Yi-Fei ^{[1
,2
]}

Xuan, Jun ^{[3
]}

Hu, Xiao-Qiang ^{[1
,2
]}

机构：

[1] South Cent Minzu Univ, Sch Chem & Mat Sci, Key Lab Catalysis & Energy Mat Chem, Wuhan 430074, Peoples R China

[2] South Cent Minzu Univ, Sch Chem & Mat Sci, Hubei Key Lab Catalysis & Mat Sci, Wuhan 430074, Peoples R China

[3] Anhui Univ, Coll Chem & Chem Engn, Anhui Prov Key Lab Chem Inorgan Organ Hybrid Funct, Hefei 230601, Anhui, Peoples R China

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 19卷

基金：

中国国家自然科学基金;

关键词：

C-H activation; enaminone; iodonium ylide; isocoumarin; rhodium catalysis; BENZOIC-ACIDS; FUNCTIONALIZATION; CYCLIZATION; ANNULATION; PHOTOREDOX; SYNTHONS; ACCESS;

D O I：

10.3762/bjoc.19.10

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report an unprecedented Rh(III)-catalyzed C-H activation/annulation cascade of readily available enaminones with iodonium ylides towards the convenient synthesis of isocoumarins. This coupling system proceeds in useful chemical yields (up to 93%) via a cascade C-H activation, Rh-carbenoid migratory insertion and acid-promoted intramolecular annulation. The success of gram-scale reaction and diverse functionalization of isocoumarins demonstrated the synthetic utility of this protocol.

引用

收藏

页码：100 / 106

页数：7

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