TY - JOUR
T1 - A facile palladium-catalyzed route to 2,5,7-trisubstituted indoles
AU - Cacchi, Sandro
AU - Fabrizi, Giancarlo
AU - Goggiamani, Antonella
AU - Iazzetti, Antonia
AU - Verdiglione, Rosanna
PY - 2015
Y1 - 2015
N2 - A facile and general approach to the synthesis of 2,5,7-trisubstituted indoles from readily available 2-bromo-6-iodo-4-substituted and 2-bromo-4-chloro-6-iodoanilines is reported. The assembly of the indole rings is accomplished via a one-pot Sonogashira cross-coupling with terminal alkynes followed by a palladium-catalyzed cyclization step. The functionalization at C7 and at C5 (with indoles bearing a chloro substituent at C5) is carried out by alkynylations, Suzuki-Miyaura cross-couplings, and Buchwald-Hartwig C-N bond forming reactions. One-pot protocols for the synthesis of 2,5,7-trisubstituted indoles from 2-aryl-7-bromo-5-chloroindoles as well as from 2-bromo-4-chloro-6-iodoaniline are also described.
AB - A facile and general approach to the synthesis of 2,5,7-trisubstituted indoles from readily available 2-bromo-6-iodo-4-substituted and 2-bromo-4-chloro-6-iodoanilines is reported. The assembly of the indole rings is accomplished via a one-pot Sonogashira cross-coupling with terminal alkynes followed by a palladium-catalyzed cyclization step. The functionalization at C7 and at C5 (with indoles bearing a chloro substituent at C5) is carried out by alkynylations, Suzuki-Miyaura cross-couplings, and Buchwald-Hartwig C-N bond forming reactions. One-pot protocols for the synthesis of 2,5,7-trisubstituted indoles from 2-aryl-7-bromo-5-chloroindoles as well as from 2-bromo-4-chloro-6-iodoaniline are also described.
KW - Cross-coupling
KW - One-pot reactions
KW - Palladium
KW - Polysubstituted indoles
KW - Cross-coupling
KW - One-pot reactions
KW - Palladium
KW - Polysubstituted indoles
UR - http://hdl.handle.net/10807/200523
U2 - 10.1016/j.tet.2015.10.002
DO - 10.1016/j.tet.2015.10.002
M3 - Article
SN - 0040-4020
VL - 71
SP - 9346
EP - 9356
JO - Tetrahedron
JF - Tetrahedron
ER -