2026-07-10T06:27:53Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/39122022-12-20T10:37:51Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594
Synthesis of diverse indole-containing scaffolds by gold(I)-catalyzed tandem reactions of 3-propargylindoles initiated by 1,2-indole migrations: scope and computational studies
Sanz Díez, Roberto
Miguel, Delia
Gohain, Mukut
García García, Patricia
Fernández Rodríguez, Manuel A.
González Pérez, Adán
Nieto Faza, Olalla .
Rodríguez de Lera, Ángel
Rodríguez, Félix
gold
homogeneous catalysis
reaction mechanism
DFT calculations
indoles
Similar to propargylic
carboxylates and sulphides, 3-
propargylindoles undergo 1,2-indole
migrations under cationic gold(I)-
catalysis. The intermediate Aucarbenoid
complex may evolve through
different pathways depending on the
substituents at the propargylic and
terminal positions of the alkyne moiety.
Thus, 3-indenylindole derivatives were
easily obtained through formal iso-
Nazarov or Nazarov cyclizations. DFT
computations support the formation of
an alkylidenecyclopropane intermediate
that undergoes aura-iso-Nazarov or
aura-Nazarov cyclizations upon
torquoselective ring opening. In
addition, 3-dienylindoles could be
accessed when none of the referred
pathways were accessible and so the
intermediate Au-carbenoid complex
evolved via a 1,2-CH insertion
reaction. We have also demonstrated
that the final products can be obtained
in a one-pot protocol from easily
available propargylic alcohols and
indoles
2016-01-27
2016-01-27
2010-08
info:eu-repo/semantics/article
0947-6539
http://hdl.handle.net/10259/3912
10.1002/chem.201001162
eng
Chemistry-A european journal. 2010, V. 16, n. 32, p. 9818-9828
http://dx.doi.org/10.1002/chem.201001162
info:eu-repo/grantAgreement/MEC-FEDER/CTQ2007-61436/BQU
info:eu-repo/grantAgreement/JCyL/BU021A09
info:eu-repo/semantics/openAccess
Wiley-VCH Verlag