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

Mengdan Wang; Lingkai Kong; Ye Wang; Bo Song; Yue Sun; Rong Tang; Yanzhong Li

doi:10.1021/acs.orglett.8b02580

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

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

Authors

Mengdan Wang¹, Lingkai Kong¹, Ye Wang¹, Bo Song¹, Yue Sun¹, Rong Tang¹, Yanzhong Li¹

Affiliation

¹ 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.

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

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 Cs₂CO₃-promoted C-C σ-bond cleavage of cyclic ketoesters and a ZnI₂-mediated selective C-H/O-H coupling reaction. Two of the C-C σ-bonds are cleaved and one of the sp² 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.

Publication types

Research Support, Non-U.S. Gov't