Palladium‐Catalyzed C—C Bond Activation/Suzuki Reaction of Methylenecyclobutanes

Main observation and conclusion Transition‐metal catalyzed C—C bond activation is a formidable challenge owing to the high bond energy. We report here a novel palladium‐catalyzed C—C bond activation manner of methylenecyclobutanes followed by subsequent Suzuki cross‐coupling reaction affording multi...

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Bibliographic Details
Published in:Chinese journal of chemistry 2021-06, Vol.39 (6), p.1611-1615
Main Authors: Chen, Xiao‐Bing, Li, Li, Yang, Wan‐Chun, Song, Kun‐Long, Wu, Bin, Gan, Wan‐Er, Cao, Jian, Xu, Li‐Wen
Format: Article
Language:English
Subjects:
Bond energy
Cascade chemical reactions
Chemical reactions
Cross coupling
C—C activation
C—C coupling
Fluorine
Methylenecyclobutanes
Palladium
Ring‐opening
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Summary:Main observation and conclusion Transition‐metal catalyzed C—C bond activation is a formidable challenge owing to the high bond energy. We report here a novel palladium‐catalyzed C—C bond activation manner of methylenecyclobutanes followed by subsequent Suzuki cross‐coupling reaction affording multisubstituted indanes. The tandem reaction process involves intramolecular carbopalladation of double bond, β‐carbon elimination and intermolecular trapping of the transient σ‐alkylpalladium complex with boronic acids. A new TADDOL‐derived phosphoramidite ligand bearing fluorine and silicon‐based bulky groups is found to be efficient for C—C bond activation of methylenecyclobutanes. We report here a novel palladium‐catalyzed C—C bond activation manner of methylenecyclobutanes followed by subsequent Suzuki cross‐coupling reaction affording multisubstituted indanes. The tandem reaction process involves intramolecular carbopalladation of double bond, β‐carbon elimination and intermolecular trapping of the transient σ‐alkylpalladium complex with boronic acids.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.202000700