Synthesis of Free NH 2-(Aminomethyl)indoles through Copper-Catalyzed Reaction of 3-(ortho-Trifluoroacetamidophenyl)-1-propargylic Alcohols with Amines and Palladium/Copper- Cocatalyzed Domino Three-Component Sonogashira Cross-Coupling/Cyclization/Substitu

Sandro Cacchi; Giancarlo Fabrizi; Antonia Iazzetti; Carmela Molinaro; Rosanna Verdiglione; Antonella Goggiamani

doi:10.1002/adsc.201400881

Synthesis of Free NH 2-(Aminomethyl)indoles through Copper-Catalyzed Reaction of 3-(ortho-Trifluoroacetamidophenyl)-1-propargylic Alcohols with Amines and Palladium/Copper- Cocatalyzed Domino Three-Component Sonogashira Cross-Coupling/Cyclization/Substitu

Sandro Cacchi
, Giancarlo Fabrizi
, Antonia Iazzetti
, Carmela Molinaro
, Rosanna Verdiglione
, Antonella Goggiamani^*

^*Autore corrispondente per questo lavoro

University of Rome La Sapienza

Risultato della ricerca: Contributo in rivista › Articolo

Abstract

Free NH 2-(aminomethyl) indoles have been prepared via copper-catalyzed cyclization of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols in the presence of primary or secondary amines. The synthesis has been developed into a simple and very efficient domino three-component Sonogashira cross-coupling/cyclization/substitution process that, omitting the isolation of 3(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols, provides access to this class of compounds by treating 2-iodotrifluoroacetanilides, propargylic alcohols, and primary or secondary amines with a copper/palladium catalyst system.

Lingua originale	Inglese
pagine (da-a)	1053-1059
Numero di pagine	7
Rivista	Advanced Synthesis and Catalysis
Volume	357
Numero di pubblicazione	5
DOI	https://doi.org/10.1002/adsc.201400881
Stato di pubblicazione	Pubblicato - 2015

All Science Journal Classification (ASJC) codes

Catalisi
Chimica Organica

Keywords

2-(aminomethyl)indoles
copper catalysis
domino reactions
multicomponent processes
palladium catalysis

Accesso al documento

10.1002/adsc.201400881

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Cacchi, S., Fabrizi, G., Iazzetti, A., Molinaro, C., Verdiglione, R., & Goggiamani, A. (2015). Synthesis of Free NH 2-(Aminomethyl)indoles through Copper-Catalyzed Reaction of 3-(ortho-Trifluoroacetamidophenyl)-1-propargylic Alcohols with Amines and Palladium/Copper- Cocatalyzed Domino Three-Component Sonogashira Cross-Coupling/Cyclization/Substitu. Advanced Synthesis and Catalysis, 357(5), 1053-1059. https://doi.org/10.1002/adsc.201400881

Cacchi, Sandro ; Fabrizi, Giancarlo ; Iazzetti, Antonia et al. / Synthesis of Free NH 2-(Aminomethyl)indoles through Copper-Catalyzed Reaction of 3-(ortho-Trifluoroacetamidophenyl)-1-propargylic Alcohols with Amines and Palladium/Copper- Cocatalyzed Domino Three-Component Sonogashira Cross-Coupling/Cyclization/Substitu. In: Advanced Synthesis and Catalysis. 2015 ; Vol. 357, N. 5. pagg. 1053-1059.

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title = "Synthesis of Free NH 2-(Aminomethyl)indoles through Copper-Catalyzed Reaction of 3-(ortho-Trifluoroacetamidophenyl)-1-propargylic Alcohols with Amines and Palladium/Copper- Cocatalyzed Domino Three-Component Sonogashira Cross-Coupling/Cyclization/Substitu",

abstract = "Free NH 2-(aminomethyl) indoles have been prepared via copper-catalyzed cyclization of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols in the presence of primary or secondary amines. The synthesis has been developed into a simple and very efficient domino three-component Sonogashira cross-coupling/cyclization/substitution process that, omitting the isolation of 3(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols, provides access to this class of compounds by treating 2-iodotrifluoroacetanilides, propargylic alcohols, and primary or secondary amines with a copper/palladium catalyst system.",

keywords = "2-(aminomethyl)indoles, copper catalysis, domino reactions, multicomponent processes, palladium catalysis, 2-(aminomethyl)indoles, copper catalysis, domino reactions, multicomponent processes, palladium catalysis",

author = "Sandro Cacchi and Giancarlo Fabrizi and Antonia Iazzetti and Carmela Molinaro and Rosanna Verdiglione and Antonella Goggiamani",

year = "2015",

doi = "10.1002/adsc.201400881",

language = "English",

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Cacchi, S, Fabrizi, G, Iazzetti, A, Molinaro, C, Verdiglione, R & Goggiamani, A 2015, 'Synthesis of Free NH 2-(Aminomethyl)indoles through Copper-Catalyzed Reaction of 3-(ortho-Trifluoroacetamidophenyl)-1-propargylic Alcohols with Amines and Palladium/Copper- Cocatalyzed Domino Three-Component Sonogashira Cross-Coupling/Cyclization/Substitu', Advanced Synthesis and Catalysis, vol. 357, n. 5, pagg. 1053-1059. https://doi.org/10.1002/adsc.201400881

Synthesis of Free NH 2-(Aminomethyl)indoles through Copper-Catalyzed Reaction of 3-(ortho-Trifluoroacetamidophenyl)-1-propargylic Alcohols with Amines and Palladium/Copper- Cocatalyzed Domino Three-Component Sonogashira Cross-Coupling/Cyclization/Substitu. / Cacchi, Sandro; Fabrizi, Giancarlo; Iazzetti, Antonia et al.
In: Advanced Synthesis and Catalysis, Vol. 357, N. 5, 2015, pag. 1053-1059.

Risultato della ricerca: Contributo in rivista › Articolo

TY - JOUR

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AU - Cacchi, Sandro

AU - Fabrizi, Giancarlo

AU - Iazzetti, Antonia

AU - Molinaro, Carmela

AU - Verdiglione, Rosanna

AU - Goggiamani, Antonella

PY - 2015

Y1 - 2015

N2 - Free NH 2-(aminomethyl) indoles have been prepared via copper-catalyzed cyclization of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols in the presence of primary or secondary amines. The synthesis has been developed into a simple and very efficient domino three-component Sonogashira cross-coupling/cyclization/substitution process that, omitting the isolation of 3(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols, provides access to this class of compounds by treating 2-iodotrifluoroacetanilides, propargylic alcohols, and primary or secondary amines with a copper/palladium catalyst system.

AB - Free NH 2-(aminomethyl) indoles have been prepared via copper-catalyzed cyclization of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols in the presence of primary or secondary amines. The synthesis has been developed into a simple and very efficient domino three-component Sonogashira cross-coupling/cyclization/substitution process that, omitting the isolation of 3(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols, provides access to this class of compounds by treating 2-iodotrifluoroacetanilides, propargylic alcohols, and primary or secondary amines with a copper/palladium catalyst system.

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KW - multicomponent processes

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KW - 2-(aminomethyl)indoles

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KW - domino reactions

KW - multicomponent processes

KW - palladium catalysis

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Cacchi S, Fabrizi G, Iazzetti A, Molinaro C, Verdiglione R, Goggiamani A. Synthesis of Free NH 2-(Aminomethyl)indoles through Copper-Catalyzed Reaction of 3-(ortho-Trifluoroacetamidophenyl)-1-propargylic Alcohols with Amines and Palladium/Copper- Cocatalyzed Domino Three-Component Sonogashira Cross-Coupling/Cyclization/Substitu. Advanced Synthesis and Catalysis. 2015;357(5):1053-1059. doi: 10.1002/adsc.201400881