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Gold(I)‐Catalyzed [8+2]‐Cycloaddition of 8‐Aryl‐8‐azaheptafulvenes with Allenamides and Ynamides: Regioselective Synthesis of Dihydrocycloheptapyrrole Derivatives
Author(s) -
SuárezRodríguez Tatiana,
SuárezSobrino Ángel L.,
Ballesteros Alfredo
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202005348
Subject(s) - regioselectivity , cycloaddition , allene , alkyne , aryl , chemistry , catalysis , nucleophile , combinatorial chemistry , nucleophilic addition , medicinal chemistry , organic chemistry , alkyl
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‐di t BuC 6 H 3 O) 3 PAuNTf 2 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 JohnPhosAuNTf 2 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.