Regioselective Hydroalkylation and Arylalkylation of Alkynes by Photoredox/Nickel Dual Catalysis: Application and Mechanism

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Abstract: Alkynes are an important class of organic molecules due to their utility as versatile building blocks in synthesis. Although efforts have been devoted to the difunctionalization of alkynes, general and practical strategies for the direct hydroalkylation and alkylarylation of terminal alkynes under mild reaction conditions are less explored. Herein, we report a photoredox/nickel dual‐catalyzed anti‐Markovnikov‐type hydroalkylation of terminal alkynes as well as a one‐pot arylalkylation of alkynes with alkyl carboxylic acids and aryl bromides via a three‐component cross‐coupling. The results indicate that the transformations proceed via a new mechanism involving a single‐electron transfer with subsequent energy‐transfer activation pathways. Moreover, steady‐state and time‐resolved fluorescence‐spectroscopy measurements, density functional theory (DFT) calculations, and wavefunction analysis have been performed to give an insight into the catalytic cycle.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Regioselective Hydroalkylation and Arylalkylation of Alkynes by Photoredox/Nickel Dual Catalysis: Application and Mechanism ; volume:59 ; number:14 ; year:2020 ; pages:5738-5746 ; extent:9
Angewandte Chemie / International edition. International edition ; 59, Heft 14 (2020), 5738-5746 (gesamt 9)

Creator: Yue, Huifeng
Zhu, Chen
Kancherla, Rajesh
Liu, Fangying
Rueping, Magnus

DOI: 10.1002/anie.201914061

URN: urn:nbn:de:101:1-2022061211193527648536

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:31 AM CEST

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Associated

Yue, Huifeng
Zhu, Chen
Kancherla, Rajesh
Liu, Fangying
Rueping, Magnus

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