Sequential C-C σ-Bond Cleavage/(sp2) C-O Bond Formation via C-H Functionalization toward Pyranoindolones Fused with Medium-Sized Rings

被引：30

作者：

Wang, Mengdan ^{[1
]}

Kong, Lingkai ^{[1
]}

Wang, Ye ^{[1
]}

Song, Bo ^{[1
]}

Sun, Yue ^{[1
]}

Tang, Rong ^{[1
]}

Li, Yanzhong ^{[1
]}

机构：

[1] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, 500 Dongchuan Rd, Shanghai 200241, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 19期

基金：

中国国家自然科学基金;

关键词：

PROMOTED TANDEM REACTION; CHROMONE DERIVATIVES; SELECTIVE FUNCTIONALIZATION; ORGANOMETALLIC CHEMISTRY; EFFICIENT SYNTHESIS; INSERTION REACTION; ROOM-TEMPERATURE; SINGLE-BOND; CARBON; ACTIVATION;

D O I：

10.1021/acs.orglett.8b02580

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An atom-economical procedure for the synthesis of pyranoindolones fused with 7- or 8-membered rings has been developed. This process is realized through the sequential Cs2CO3-promoted C-C sigma-bond cleavage of cyclic ketoesters and a ZnI2-mediated selective C-H/O-H coupling reaction. Two of the C-C sigma-bonds are cleaved and one of the sp(2) C-H bonds is functionalized during the reaction process. Easily accessible starting materials and broad substrate scope make this protocol attractive in synthetic organic chemistry.

引用

页码：6130 / 6134

页数：5

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