Oxidative Gold Catalysis Meets Photochemistry – Synthesis of Benzo[a]fluorenones from Diynes. Issue 18 (14th November 2014)

• Record Type: Journal Article
• Authors: Nösel, Pascal; Moghimi, Setareh; Hendrich, Christoph; Haupt, Marten; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K.
• Is Part Of: Advanced synthesis & catalysis. Volume 356:Issue 18(2014)
• Page Start: 3755
• Page End: 3760
• Publication Date: 2014-11-14
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201400969
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Diynes bearing one terminal and one triarylmethyl‐substituted alkyne were converted into complex benzofluorenone derivatives <italic>via</italic> a one‐pot process involving a gold‐catalyzed step followed by a photocyclization/oxidation. In the first step an <italic>N</italic>‐oxide was used to position‐selectively generate an α‐oxo carbenoid at the terminal alkyne which after a regioselective 1, 6‐carbene transfer along the tethered tritylalkyne and a subsequent aryl 1, 2‐shift furnished tetraphenylethylene‐like derivatives. These intermediates were successfully transformed to fluorenones <italic>via</italic> oxidative photocyclization.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgh2qst2pww" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>