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Oxidative Gold Catalysis Meets Photochemistry – Synthesis of Benzo[ a ]fluorenones from Diynes
Author(s) -
Nösel Pascal,
Moghimi Setareh,
Hendrich Christoph,
Haupt Marten,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400969
Subject(s) - chemistry , regioselectivity , carbenoid , alkyne , carbene , aryl , photochemistry , tetraphenylethylene , catalysis , combinatorial chemistry , organic chemistry , rhodium , alkyl , physics , fluorescence , quantum mechanics , aggregation induced emission
Diynes bearing one terminal and one triarylmethyl‐substituted alkyne were converted into complex benzofluorenone derivatives via a one‐pot process involving a gold‐catalyzed step followed by a photocyclization/oxidation. In the first step an N ‐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 via oxidative photocyclization.