Issue 4, 2023

Inherently chiral calixarenes by a catalytic enantioselective desymmetrizing cross-dehydrogenative coupling

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.

Graphical abstract: Inherently chiral calixarenes by a catalytic enantioselective desymmetrizing cross-dehydrogenative coupling

Supplementary files

Article information

Article type
Edge Article
Submitted
11 Nov. 2022
Accepted
05 Dec. 2022
First published
06 Dec. 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 827-832

Inherently chiral calixarenes by a catalytic enantioselective desymmetrizing cross-dehydrogenative coupling

X. Zhang, S. Tong, J. Zhu and M. Wang, Chem. Sci., 2023, 14, 827 DOI: 10.1039/D2SC06234H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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