RT info:eu-repo/semantics/article
T1 Brønsted Acid Catalyzed Alkylation of Indoles with Tertiary Propargylic Alcohols: Scope and Limitations
A1 Sanz Díez, Roberto
A1 Miguel, Delia
A1 Martínez Cuezva, Alberto
A1 Gohain, Mukut
A1 García García, Patricia
A1 Fernández Rodríguez, Manuel A.
A1 Álvarez Manuel, Estela
A1 Rodríguez, Félix
K1 Indoles
K1 Alkylation
K1 Brønsted acids
K1 Alcohols
K1 Nucleophilic substitution
K1 Química orgánica
K1 Chemistry, Organic
AB Direct alkylation of indoles with a wide variety of tertiary propargylic alcohols under Brønsted acid catalysis conditions has been studied. A general and environmentally friendly method for the synthesis of 3-propargylated indoles with quaternary carbon atoms at their propargylic positions has been developed. The reactions are highly regioselective with regard both to the indole and to the alkynol components. Only with N-unsubstituted 2-arylindoles do competitive SN′ reactions take place to afford 3-dienyl- or 3-allenylindoles, depending on the alkynol moiety. The reactions were carried out in air with undried solvents, and water was the only side product.
PB Wiley-VCH Verlag
SN 1434-193X
YR 2010
FD 2010-12
LK http://hdl.handle.net/10259/3864
UL http://hdl.handle.net/10259/3864
LA eng
NO Junta de Castilla y Leon (BU021A09 and GR-172) and the Ministerio de Educacion y Ciencia (MEC) and FEDER (CTQ2007-61436/BQU and CTQ2009-09949/BQU) for financial support. D. M. and A. M. thank the MEC for MEC-FPU predoctoral fellowships. M. G. thanks the MEC for a "Young Foreign Researchers" contract (SB2006-0215). M. A. F.-R. and P. G.-G. also thank the MEC for "Ramon y Cajal" and "Juan de la Cierva" contracts.
DS Repositorio Institucional de la Universidad de Burgos
RD 24-abr-2024