Alkyne Difunctionalization by Dual Gold/Photoredox Catalysis. Issue 17 (8th March 2016)

• Record Type: Journal Article
• Authors: Tlahuext‐Aca, Adrian; Hopkinson, Matthew N.; Garza‐Sanchez, R. Aleyda; Glorius, Frank
• Is Part Of: Chemistry. Volume 22:Issue 17(2016)
• Page Start: 5909
• Page End: 5913
• Publication Date: 2016-03-08
• Subjects: alkynes -- arylation -- diazonium salts -- gold -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201600710
• Languages: English
• ISSNs: 0947-6539

Abstract

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 Au I 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. Abstract : 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.