RT info:eu-repo/semantics/article
T1 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
A1 Sanz Díez, Roberto
A1 Miguel, Delia
A1 Gohain, Mukut
A1 García García, Patricia
A1 Fernández Rodríguez, Manuel A.
A1 González Pérez, Adán
A1 Nieto Faza, Olalla .
A1 Rodríguez de Lera, Ángel
A1 Rodríguez, Félix
K1 gold
K1 homogeneous catalysis
K1 reaction mechanism
K1 DFT calculations
K1 indoles
K1 Química orgánica
K1 Chemistry, Organic
AB Similar to propargyliccarboxylates and sulphides, 3-propargylindoles undergo 1,2-indolemigrations under cationic gold(I)-catalysis. The intermediate Aucarbenoidcomplex may evolve throughdifferent pathways depending on thesubstituents at the propargylic andterminal positions of the alkyne moiety.Thus, 3-indenylindole derivatives wereeasily obtained through formal iso-Nazarov or Nazarov cyclizations. DFTcomputations support the formation ofan alkylidenecyclopropane intermediatethat undergoes aura-iso-Nazarov oraura-Nazarov cyclizations upontorquoselective ring opening. Inaddition, 3-dienylindoles could beaccessed when none of the referredpathways were accessible and so theintermediate Au-carbenoid complexevolved via a 1,2-CH insertionreaction. We have also demonstratedthat the final products can be obtainedin a one-pot protocol from easilyavailable propargylic alcohols andindoles
PB Wiley-VCH Verlag
SN 0947-6539
YR 2010
FD 2010-08
LK http://hdl.handle.net/10259/3912
UL http://hdl.handle.net/10259/3912
LA eng
NO MEC/FEDER (CTQ2007-61436/BQU) and Junta de Castilla y León (BU021A09) for financial support. We are also grateful to MEC (FPU predoctoral fellowship to D.M., “Young Foreign Researchers” contract (SB2006-0215) to M.G., “Ramón y Cajal” contract to M.A.F.-R., and “Juan de la Cierva” contract to P.G.-G.) and Fundación Ramón Areces (predoctoral fellowship to A.G.P.).
DS Repositorio Institucional de la Universidad de Burgos
RD 22-nov-2024