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Issue 23, 2020
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Cu-Photoredox-catalyzed C(sp)–C(sp3) coupling of redox-active esters with terminal alkynes

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Abstract

Visible-light-induced C(sp)–C(sp3) coupling of redox-active esters with terminal alkynes has been developed. The activation of carboxylic acids as their redox-active ester derivatives was important for this decarboxylative alkynylation. The strategy established here facilitates the straightforward introduction of triple-bonded functional groups and avoids additional photocatalysts. A wide range of primary, secondary and tertiary acids can be converted into the target products; so this reaction exhibits a broad substrate scope and tolerance of functional groups. Mechanistic experiments suggested that this reaction may undergo a radical process. Under mild reaction conditions, a copper acetylide ligand as a photocatalyst delivered an electron to redox-active ester derivatives, and generated alkyl radicals. The radicals reacted with Cu(II) to deliver a Cu(III) complex, and then reductive elimination gave the products.

Graphical abstract: Cu-Photoredox-catalyzed C(sp)–C(sp3) coupling of redox-active esters with terminal alkynes

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Supplementary files

Article information


Submitted
22 Apr 2020
Accepted
18 May 2020
First published
19 May 2020

Org. Biomol. Chem., 2020,18, 4479-4483
Article type
Paper

Cu-Photoredox-catalyzed C(sp)–C(sp3) coupling of redox-active esters with terminal alkynes

Y. Zhang and D. Zhang, Org. Biomol. Chem., 2020, 18, 4479
DOI: 10.1039/D0OB00835D

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