Products Cited in Publications Worldwide Site-selective C–H functionalization in a cyclodextrin metal-organic framework

Site-selective C–H functionalization in a cyclodextrin metal-organic framework

Aspen X.-Y. Chen; Tanay Kesharwani Yong Wu; Haoyuan Chen; Dengke Shen; J. Fraser Stoddart

DOI:

Abstract

Confinement is a unifying element in selective enzymic reactions but has rarely been used to control site selectivity of carbon-hydrogen (C-H) bond functionalization in artificial receptors. Herein, we demonstrate the selective functionalization of one of seven C(sp3)-H bonds on a D-glucopyranosyl residue of (γ-CD) by irradiating 2-benzoylbenzoate in a γ-cyclodextrin-containing metal-organic framework (CD-MOF-1). Both 1H NMR spectroscopy and X-ray crystallog. of the products confirm that functionalization occurs selectively at one of the two C(sp3)-H bonds on the C6 position of a D-glucopyranosyl residue. The alignment of 2-benzoylbenzoate inside (γ-CD)2 tunnels in CD-MOF-1, as revealed by X-ray crystallog., precludes C-H functionalization on the outer surface of the γ-CD tori. Theoretical calculations indicate less steric hindrance associated with C6-functionalized (γ-CD)2 tunnels in CD-MOF-1 compared with C3 and C5, leading to the observed site selectivity.

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2-Benzoylbenzoic acid

A83375385-52-998%

2-Benzoylbenzoic acid

21.0/100g

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