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Photoinduced Gold-Catalyzed Domino C(sp) Arylation/Oxyarylation of TMS-Terminated Alkynols with Arenediazonium Salts

AuthorsAlcaide, Benito ; Almendros, Pedro ; Busto, Eduardo; Lázaro-Milla, Carlos
Issue Date2017
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 82: 2177-2186 (2017)
AbstractA selective and convenient synthesis of tri- and tetrasubstituted α,β-unsaturated ketones, as well as 2,3-diarylbenzofurans has been developed with the aid of light and taking advantage of a cooperative gold/photoredox-catalyzed 2-fold arylation reaction of TMS-terminated alkynols. The reaction of 3-(trimethylsilyl)prop-2-yn-1-ols was competent to generate diarylated α,β-unsaturated ketones; whereas the photoredox sequence involving 2-[(trimethylsilyl)ethynyl]phenol exclusively afforded 2,3-diarylbenzofurans. The reaction of terminal alkynes proceeded in poor yields while the use of bulkier silyl groups, such as TIPS, resulted unproductive. Apparently, the C(sp) arylation reaction is the first event on the domino bis-arylative sequence. These results could be explained through the intermediation of arylgold(III) species and several single electron transfer processes.
Publisher version (URL)http://dx.doi.org/10.1021/acs.joc.6b03006
Identifiersdoi: 10.1021/acs.joc.6b03006
issn: 0022-3263
e-issn: 1520-6904
Appears in Collections:(IQOG) Artículos
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