Work

Scalable deoxygenative alkynylation of alcohols via flow photochemistry

Year: 2024

Type: article

Abstract: Internal alkynes are often contained in bioactive pharmaceuticals and crucial intermediates in material sciences, yet their production methods are often limited and challenging, necessitating the development of more efficient and versatile synthetic routes. Here we report a method of deoxygenative alkynylation of alcohols via flow photochemistry. Formation of N-heterocyclic carbene-alcohol adducts undergoes oxidation by a photocatalyst, generating alkyl radicals. These radicals are subsequently trapped by an alkynylation agent, yielding the desired alkyne. Compared to batch reactions, the strategy using flow photochemistry is practical and efficient to complete the reaction in relatively short time with good yields. A wide range of functional groups were tolerated. The broad application of this method for alkyne synthesis in industry settings is anticipated, supported by the potential in late-stage functionalization of biomolecules and gram-scale synthesis.

Source: Communications Chemistry

DOI: 10.1038/s42004-024-01363-4

Authors: Pin Xu, Cong Ma

Institution: Hong Kong Polytechnic University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,690

Funders: Research Grants Council, University Grants Committee, Hong Kong Polytechnic University