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

被引：25
|
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
收藏
页码：6130 / 6134
页数：5
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