Alkyne difunctionalization by dual gold/photoredox catalysis

A Tlahuext‐Aca, MN Hopkinson… - … A European Journal, 2016 - Wiley Online Library
A Tlahuext‐Aca, MN Hopkinson, RA Garza‐Sanchez, F Glorius
Chemistry–A European Journal, 2016Wiley Online Library
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 …
Abstract
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.
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