Inherently chiral calixarenes by a catalytic enantioselective desymmetrizing cross-dehydrogenative coupling
Literature Information
Publication Date
2022-12-06
DOI
10.1039/D2SC06234H
Impact Factor
9.825
Authors
Xin Zhang, Shuo Tong, Jieping Zhu, Mei-Xiang Wang
View Original
Abstract
Under the catalysis of PdBr2 and a chiral phosphoramidite ligand, the upper-rim mono (2-bromoaroyl)-substituted calix[4]arene derivatives underwent a facile enantioselective desymmetrization reaction to afford 9H-fluorene-embedded inherently chiral calixarenes in good yields with excellent enantioselectivities. The transannular dehydrogenative arene–arene coupling reaction proceeded most probably through an oxidative addition of the Caryl–Br bond to a ligated palladium catalyst followed by a sequence of an enantioselective 1,5-palladium migration and an intramolecular C–H arylation sequence. This new family of inherently chiral calixarenes possesses unique chiroptical properties thanks to their highly rigid structure induced by the 9H-fluorene segment.
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