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Gold(I)-Catalyzed [8+2]-Cycloaddition of 8-Aryl-8-azaheptafulvenes with Allenamides and Ynamides: Regioselective Synthesis of Dihydrocycloheptapyrrole Derivatives.

Tatiana Suárez-RodríguezÁngel L Suárez-SobrinoAlfredo Ballesteros
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2021)
Gold(I)-catalyzed higher-order [8+2] cycloadditions of 8-aryl-8-azaheptafulvenes 1 with allenamides 2 and ynamides 3 were studied. 1,8-Dihydrocycloheptapyrroles 4 were achieved by a regioselective [8+2] cycloaddition of azaheptafulvenes 1 and allenamides 2 in the presence of (2,4-ditBuC6 H3 O)3 PAuNTf2 as catalyst. Besides, ynamides 3 and 8-aryl-8-azaheptafulvenes 1, undergo a regioselective [8+2] cycloaddition, to give 2-amido-1,4-dihydrocycloheptapyrroles 7 in the presence of JohnPhosAuNTf2 as catalyst. Both reactions take place with good yields and with a variety of substituents. A plausible mechanism hypothesis suggests a nucleophilic attack of the 8-azaheptafulvene to the gold activated electron rich allene or alkyne moieties of the allenamide and ynamide, respectively.
Keyphrases
  • room temperature
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  • visible light
  • electron microscopy