Copper-catalyzed coupling of N -tosylhydrazones with amines: Synthesis of fluorene derivatives

Jessy Aziz; Gilles Frison; Montserrat Gómez; Jean Daniel Brion; Abdallah Hamze; Mouad Alami

doi:10.1021/cs5014877

Copper-catalyzed coupling of N -tosylhydrazones with amines: Synthesis of fluorene derivatives

Jessy Aziz
, Gilles Frison
, Montserrat Gómez
, Jean Daniel Brion
, Abdallah Hamze
, Mouad Alami

École Polytechnique

Université Paris-Saclay
Centre national de la recherche scientifique

Research output: Contribution to journal › Article › peer-review

Abstract

An original formation of one C-N bond and one C-C bond on the same carbenic center has been developed. This approach involves a copper-catalyzed cross-coupling reaction between 2'-bromo-biaryl-N-tosylhydrazones and different amines leading to 9H-fluoren-9-amine derivatives. This reaction proceeds under mild conditions in glycerol, an inexpensive and environmentally friendly solvent, without adding any external ligand.

Original language	English
Pages (from-to)	4498-4503
Number of pages	6
Journal	ACS Catalysis
Volume	4
Issue number	12
DOIs	https://doi.org/10.1021/cs5014877
Publication status	Published - 5 Dec 2014

Keywords

C-N/C-C bond formation
N -tosylhydrazones
autotandem catalysis
carbenoid
fluoren-9 H -amines

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10.1021/cs5014877

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title = "Copper-catalyzed coupling of N -tosylhydrazones with amines: Synthesis of fluorene derivatives",

abstract = "An original formation of one C-N bond and one C-C bond on the same carbenic center has been developed. This approach involves a copper-catalyzed cross-coupling reaction between 2'-bromo-biaryl-N-tosylhydrazones and different amines leading to 9H-fluoren-9-amine derivatives. This reaction proceeds under mild conditions in glycerol, an inexpensive and environmentally friendly solvent, without adding any external ligand.",

keywords = "C-N/C-C bond formation, N -tosylhydrazones, autotandem catalysis, carbenoid, fluoren-9 H -amines",

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note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

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language = "English",

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T2 - Synthesis of fluorene derivatives

AU - Aziz, Jessy

AU - Frison, Gilles

AU - Gómez, Montserrat

AU - Brion, Jean Daniel

AU - Hamze, Abdallah

AU - Alami, Mouad

PY - 2014/12/5

Y1 - 2014/12/5

N2 - An original formation of one C-N bond and one C-C bond on the same carbenic center has been developed. This approach involves a copper-catalyzed cross-coupling reaction between 2'-bromo-biaryl-N-tosylhydrazones and different amines leading to 9H-fluoren-9-amine derivatives. This reaction proceeds under mild conditions in glycerol, an inexpensive and environmentally friendly solvent, without adding any external ligand.

AB - An original formation of one C-N bond and one C-C bond on the same carbenic center has been developed. This approach involves a copper-catalyzed cross-coupling reaction between 2'-bromo-biaryl-N-tosylhydrazones and different amines leading to 9H-fluoren-9-amine derivatives. This reaction proceeds under mild conditions in glycerol, an inexpensive and environmentally friendly solvent, without adding any external ligand.

KW - C-N/C-C bond formation

KW - N -tosylhydrazones

KW - autotandem catalysis

KW - carbenoid

KW - fluoren-9 H -amines

UR - https://www.scopus.com/pages/publications/84915753111

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DO - 10.1021/cs5014877

M3 - Article

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EP - 4503

JO - ACS Catalysis

JF - ACS Catalysis

IS - 12

ER -

Copper-catalyzed coupling of N -tosylhydrazones with amines: Synthesis of fluorene derivatives

Abstract

Keywords

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