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, SuzukieMiyaura cross-couplings, and Buchwald- Hartwig CeN 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.

A facile palladium-catalyzed route to 2,5,7-trisubstituted indoles / Cacchi, Sandro; Fabrizi, Giancarlo; Goggiamani, Antonella; Iazzetti, Antonia; Verdiglione, Rosanna. - In: TETRAHEDRON. - ISSN 0040-4020. - 71:49(2015), pp. 9346-9356. [10.1016/j.tet.2015.10.002]

A facile palladium-catalyzed route to 2,5,7-trisubstituted indoles

CACCHI, Sandro;FABRIZI, Giancarlo;GOGGIAMANI, ANTONELLA
;
IAZZETTI, Antonia;VERDIGLIONE, ROSANNA
2015

Abstract

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, SuzukieMiyaura cross-couplings, and Buchwald- Hartwig CeN 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.
cross-coupling; one-pot reactions; palladium; polysubstituted indoles; biochemistry; organic chemistry; drug discovery3003 pharmaceutical science
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A facile palladium-catalyzed route to 2,5,7-trisubstituted indoles / Cacchi, Sandro; Fabrizi, Giancarlo; Goggiamani, Antonella; Iazzetti, Antonia; Verdiglione, Rosanna. - In: TETRAHEDRON. - ISSN 0040-4020. - 71:49(2015), pp. 9346-9356. [10.1016/j.tet.2015.10.002]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/867565
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