3 years ago

Alkynylation of Csp2 (O)–H Bonds Enabled by Photoredox-Mediated Hydrogen-Atom Transfer

Alkynylation of Csp2
(O)–H Bonds Enabled by Photoredox-Mediated Hydrogen-Atom Transfer
Frank Glorius, Satobhisha Mukherjee, R. Aleyda Garza-Sanchez, Adrian Tlahuext-Aca
The development of new hydrogen-atom transfer (HAT) strategies within the framework of photoredox catalysis is highly appealing for its power to activate a desired C−H bond in the substrate leading to its selective functionalization. Reported here is the first photoredox-mediated hydrogen-atom transfer method for the efficient synthesis of ynones, ynamides, and ynoates with high regio- and chemoselectivity by direct functionalization of Csp2 (O)−H bonds. The broad synthetic application of this method has been demonstrated by the selective functionalization of C(O)−H bonds within complex molecular scaffolds. Tip your HAT: A photoredox-catalyzed hydrogen-atom transfer (HAT) method has been developed for the successful generation of carbonyl radicals from aldehydes and analogous compounds with an XC(O)−H (X=N, O) group. The successful trapping of the carbonyl radicals with ethynylbenziodoxolone (EBX) reagents provides a route for the synthesis of ynones, ynamides, and ynoates from readily available starting materials.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201708037

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