Hydrogen Bond-Controlled Site-Selective C–H Borylation at the Remote-Position of Naphthalene Derivatives

28 May 2025, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We successfully developed site-selective C–H borylation at the remote position (7-position) of naphthalene derivatives, which was controlled by hydrogen bonding between the substrate-recognition site of the catalyst (hydrogen bond donor) and the functional group of the substrate (hydrogen bond acceptor). This is the first example of site-selective C–H boryla-tion at a remote position of naphthalene and anthracene derivatives. By changing the ligands, the reaction sites can be switched, and site-selective remote C–H borylation of naphthalene derivatives with a functional group at the 1- or 2-position can be achieved.

Keywords

C-H transformation
site-selective
remote-position
hydrogen bond
C-H borylation

Supplementary materials

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Supporting Information
Description
Typical experimental procedures (synthesis of ligands and substrates, C–H borylation, gram-scale and 1 mmol-scale synthesis, and transformations of borylated product) and characterization data for C(sp3)–H borylated products
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