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通过 C-H 官能化实现稠环并吡喃吲哚酮的连续 C-C σ 键断裂/(sp)C-O 键形成。

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

机构信息

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering , East China Normal University , 500 Dongchuan Road , Shanghai 200241 , China.

出版信息

Org Lett. 2018 Oct 5;20(19):6130-6134. doi: 10.1021/acs.orglett.8b02580. Epub 2018 Sep 14.

DOI:10.1021/acs.orglett.8b02580
PMID:30216080
Abstract

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 CsCO-promoted C-C σ-bond cleavage of cyclic ketoesters and a ZnI-mediated selective C-H/O-H coupling reaction. Two of the C-C σ-bonds are cleaved and one of the sp 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.

摘要

发展了一种原子经济性合成吡喃并吲哚酮与 7 或 8 元环稠合的方法。该过程通过顺序 CsCO 促进的环状酮酯的 C-C σ 键断裂和 ZnI 介导的选择性 C-H/O-H 偶联反应来实现。在反应过程中,两个 C-C σ 键被切断,一个 sp C-H 键被官能化。易得的起始原料和广泛的底物范围使该方法在合成有机化学中具有吸引力。

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