Terminal C(sp<sup>3</sup>)-H borylation through intermolecular radical sampling.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 38300993.
- Also identified by DOI 10.1126/science.adj9258.
- No licence information is recorded for this record.
- Because redistribution is not established, this page shows the abstract only. Follow the links below for the full text.
Abstract
Hydrogen atom transfer (HAT) processes can overcome the strong bond dissociation energies (BDEs) of inert C(sp<sup>3</sup>)-H bonds and thereby convert feedstock alkanes into value-added fine chemicals. Nevertheless, the high reactivity of HAT reagents, coupled with the small differences among various C(sp<sup>3</sup>)-H bond strengths, renders site-selective transformations of straight-chain alkanes a great challenge. Here, we present a photocatalytic intermolecular radical sampling process for the iron-catalyzed borylation of terminal C(sp<sup>3</sup>)-H bonds in substrates with small steric hindrance, including unbranched alkanes. Mechanistic investigations have revealed that the reaction proceeds through a reversible HAT process, followed by a selective borylation of carbon radicals. A boron-sulfoxide complex may contribute to the high terminal regioselectivity observed.