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Alkyne Difunctionalization by Dual Gold/Photoredox Catalysis

Lookup NU author(s): Dr Matt HopkinsonORCiD

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Abstract

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Highly selective tandem nucleophilic addition/cross-coupling reactions of alkynes have been developed using visible-light-promoted dual gold/photoredox catalysis. The simultaneous oxidation of AuI and coordination of the coupling partner by photo-generated aryl radicals, and the use of catalytically inactive gold precatalysts allows for high levels of selectivity for the cross-coupled products without competing hydrofunctionalization or homocoupling. As demonstrated in representative arylative Meyer-Schuster and hydration reactions, this work expands the scope of dual gold/photoredox catalysis to the largest class of substrates for gold catalysts and benefits from the mild and environmentally attractive nature of visible-light activation. United we stand! Tandem nucleophilic addition/cross-coupling reactions have been developed with challenging alkynes using a visible-light-promoted dual gold/photoredox catalytic system (see scheme). High levels of selectivity for the cross-coupled products were obtained without competition from the homocoupling or conventional hydrofunctionalization.

Publication metadata

Author(s): Tlahuext-Aca A, Hopkinson MN, Aleyda Garza-Sanchez R, Glorius F

Publication type: Article

Publication status: Published

Journal: Chemistry - A European Journal

Year: 2016

Volume: 22

Issue: 17

Pages: 5909-5913

Print publication date: 18/04/2016

Online publication date: 17/02/2016

Acceptance date: 16/02/2016

ISSN (print): 0947-6539

ISSN (electronic): 1521-3765

Publisher: Wiley-VCH Verlag

URL: https://doi.org/10.1002/chem.201600710

DOI: 10.1002/chem.201600710

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