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A Unified Platform for Direct Alkynylation from Alcohols via Deoxygenative Metallaphotoredox Catalysis
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DOI：10.1021/jacs.6c10795.png)
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Abstract
En 中文
Alkyne motifs are privileged functional groups in medicinal chemistry and serve as key handles in bioorthogonal click chemistry. Herein, we report a general metallaphotoredox deoxygenative C(sp3)–C(sp) coupling strategy that enables the direct conversion of alcohols into alkynes using alkynyl bromides as coupling partners. This protocol operates under redox-neutral, mild conditions via NHC-mediated alcohol activation and nickel catalysis, enabling the generation of alkyl radicals from alcohols and their subsequent cross-coupling with alkynyl electrophiles. The method exhibits broad substrate scope across structurally complex alcohols, including pharmaceuticals, peptides, nucleosides, and natural products, providing a practical platform for the synthesis of click-ready alkynes from readily available alcohol feedstocks. In addition, the alkynyl bromide manifold enables modular diversification and late-stage functionalization of amino acid side chains and other bioactive molecules, significantly expanding the accessible chemical space for alkyne-based medicinal and bioconjugation chemistry.
Keywords:
Addition reactions
Alcohols
Anions
Cross coupling reaction
Hydrocarbons
Journal
IF:
15.6
Papers:
20.0W
Citations:
60.2W
Organization
Cited Papers