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Site-selective C–H functionalization in a cyclodextrin metal-organic framework
Journal article   Peer reviewed

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

Aspen X.-Y. Chen, Tanay Kesharwani, Yong Wu, Charlotte L. Stern, Luka Đorđević, Huang Wu, Yu Wang, Bo Song, Liang Feng, Long Zhang, …
Chem, Vol.10(1), pp.234-249
01/2024
DOI: https://doi.org/10.1016/j.chempr.2023.08.028
Web of Science ID: WOS:001156301000001

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Abstract

Billions of years of evolution have honed nature’s extraordinary capacity in promoting site-selective functionalization of C(sp3)–H bonds in complex molecules. Central to this incredible proficiency is the effect of confinement incurred by enzymes’ active sites, which pre-organize substrates in desired co-conformations prior to their selective transformations. The fact that C(sp3)–H bonds with negligible stereoelectronic differences can be differentiated at an Ångström level during enzymatic catalysis means that precise control of site selectivities in C(sp3)–H functionalization can in principle be achieved by tailoring the cavity sizes, geometries, and stereoelectronic environments of artificial receptors. Given the importance of late-stage functionalization in drug development, there is every reason to believe that confinement, among other strategies, will become an increasingly important tool for tackling challenges in the selective editing of C(sp3)–H bonds in complex settings.

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