Synthesis of benzoheterocycles by palladium-catalyzed migratory cyclization through an unexpected reaction cascade.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 40204738.
- Also identified by DOI 10.1038/s41467-025-58633-5 and PMC identifier 11982304.
- Licence recorded as CC BY-NC-ND.
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Abstract
Migratory functionalization of C-H bonds through metal migration from carbon to carbon under transition metal catalysis is a process of significant academic and industrial interest. Herein, a palladium-catalyzed migratory cyclization of α-bromoalkene derivatives ArXCBr=CH<sub>2</sub>, in which X denotes a phosphorus (P(O)R), silicon (SiR<sub>2</sub>), sulfur (SO<sub>2</sub>), carbon (C(O)), nitrogen (NTs), or oxygen-based moiety, affording various benzoheterocyclic compounds has been developed. Mechanistic investigations have demonstrated that the cyclization reaction proceeds through an unexpected cascade, with trans-1,2-palladium migration between sp<sup>2</sup> carbons being a key step of catalytic cycle. To the best of our knowledge, this type of metal migration has not been reported previously.