4.7 Article

Photopromoted Entry to Benzothiophenes, Benzoselenophenes, 3H-Indoles, Isocoumarins, Benzosultams, and (Thio)flavones by Gold-Catalyzed Arylative Heterocyclization of Alkynes

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 15, Pages 2640-2652

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700427

Keywords

alkynes; cyclization; gold; heterocyclic compounds; synthetic methods

Funding

  1. MINECO
  2. FEDER [CTQ2015-65060-C2-1-P, CTQ2015-65060-C2-2-P]

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Visible light-promoted and gold-photoredox-catalyzed reactions of heteroatom (N, S, Se, O) tethered alkynes with arenediazonium salts selectively proceeded to build vicinal diaryl-substituted 2H-benzo[e][ 1,2] thiazine 1,1-dioxides (benzosultams), benzoselenophenes, benzothiophenes, 4H-chromen-4-ones (flavones), 3H-indoles, 1H-isochromen-1-ones (isocoumarins), and 4H-thiochromen-4-ones (thiofla-vones). Moreover, the utility of functionalized 3H-indoles as precursors for further elaboration has been demonstrated with the switchable and facile preparation of 1H-indoles, 2-oxindoles, and 3-oxindolines.

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