Authors
Qi Sun, Shuhao Li, ZhangKai Cui, Panpan Ma, Linlin Ding, Hongjian Lu
Published in
Angewandte Chemie (International ed. in English). Pages e6992524. Sep 18, 2026. Epub Sep 18, 2026.
Abstract
Nitrogen atoms play pivotal roles in governing molecular properties and biological activity. Accordingly, nitrogen-atom manipulation has emerged as a powerful strategy for skeletal remodeling. However, its integration into classical reactions to redirect their inherent pathways and outcomes remains largely unexplored. Here, we report a deaminative allylation enabled by embedding a photoinduced N-atom deletion process within a classical N-allylation reaction. This reaction-reprogramming strategy transforms ubiquitous alkylamines into α-substituted acrylates and acrylamides-privileged motifs in covalent drugs, chemical biology probes, and functional materials. Mechanistic studies reveal multiple parallel pathways, including deaminative allylation of alkylamines, formal nitrogen-atom deletion of allyl alkylamine intermediates, and denitrogenation of allyl alkyldiazene species, which collectively converge on the same products. The method exhibits broad substrate scope and excellent functional-group tolerance, enabling late-stage modification of natural products and pharmaceuticals. Beyond providing streamlined access to valuable acrylic compounds, this work establishes a pathway-convergent reaction paradigm that harnesses, rather than suppresses, competing reaction pathways, offering new opportunities for bioactive-molecule discovery.
PMID:
42757997
Bibliographic data and abstract were imported from PubMed on 18 Sep 2026.
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