Journal
CHINESE JOURNAL OF CHEMISTRY
Volume 39, Issue 6, Pages 1573-1579Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202100034
Keywords
C— C coupling; Palladium; Reduction; Indene; C— H activation
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This paper presents the first case of a reductive coupling reaction using indene as a reducing agent, showing a broad substrate scope and various types of reactions. The formation of an eta(3)-palladium indene intermediate was confirmed through control experiments and density functional theory calculations, while the formation of palladium anion intermediates was excluded.
Main observation and conclusion This paper describes the first case of a reductive coupling reaction with indene, a non-heteroatom olefin used as a reducing agent. The scope of the substrate is wide. The homo-coupling, cross-coupling, and synthesis of 12 and 14-membered rings were realized. The control experiment, indene-product curve and density functional theory calculations showed that the eta(3)-palladium indene intermediate was formed by C-H activation in the presence of cesium carbonate. We speculate that the final product was obtained through a Pd (IV) intermediate or aryl ligand exchange. In addition, we excluded the formation of palladium anion (Pd(0)(-)) intermediates.
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