Chromium(II)-catalyzed amination of N-heterocyclic chlorides with magnesium amides

Andreas K. Steib; Sarah Fernandez; Olesya M. Kuzmina; Martin Corpet; Corinne Gosmini; Paul Knochel

doi:10.1055/s-0034-1380178

Chromium(II)-catalyzed amination of N-heterocyclic chlorides with magnesium amides

Andreas K. Steib
, Sarah Fernandez
, Olesya M. Kuzmina
, Martin Corpet
, Corinne Gosmini
, Paul Knochel

Universität München
CNRS

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

Abstract

Abstract We report a ligand-free chromium(II)-catalyzed amination reaction of various N-heterocyclic chlorides. CrCl₂ regioselectively catalyzes the reaction of chloropyridines and dichloropyridines, dichloroquinolines, dichloroisoquinolines and dichloroquinoxalines with a range of aliphatic, allylic, benzylic and saturated (hetero)cyclic magnesium amides in the presence of lithium chloride as additive. The reactions were performed at 50°C in THF and led to the desired aminated products in 56-96% yield.

Original language	English
Pages (from-to)	1049-1054
Number of pages	6
Journal	Synlett
Volume	26
Issue number	8
DOIs	https://doi.org/10.1055/s-0034-1380178
Publication status	Published - 26 Feb 2015
Externally published	Yes

Keywords

Amination
Chromium
Heterocycles
Magnesium amides
Pyridine

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10.1055/s-0034-1380178

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title = "Chromium(II)-catalyzed amination of N-heterocyclic chlorides with magnesium amides",

abstract = "Abstract We report a ligand-free chromium(II)-catalyzed amination reaction of various N-heterocyclic chlorides. CrCl2 regioselectively catalyzes the reaction of chloropyridines and dichloropyridines, dichloroquinolines, dichloroisoquinolines and dichloroquinoxalines with a range of aliphatic, allylic, benzylic and saturated (hetero)cyclic magnesium amides in the presence of lithium chloride as additive. The reactions were performed at 50°C in THF and led to the desired aminated products in 56-96\% yield.",

keywords = "Amination, Chromium, Heterocycles, Magnesium amides, Pyridine",

author = "Steib, \{Andreas K.\} and Sarah Fernandez and Kuzmina, \{Olesya M.\} and Martin Corpet and Corinne Gosmini and Paul Knochel",

note = "Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart.",

year = "2015",

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day = "26",

doi = "10.1055/s-0034-1380178",

language = "English",

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journal = "Synlett",

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TY - JOUR

T1 - Chromium(II)-catalyzed amination of N-heterocyclic chlorides with magnesium amides

AU - Steib, Andreas K.

AU - Fernandez, Sarah

AU - Kuzmina, Olesya M.

AU - Corpet, Martin

AU - Gosmini, Corinne

AU - Knochel, Paul

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart.

PY - 2015/2/26

Y1 - 2015/2/26

N2 - Abstract We report a ligand-free chromium(II)-catalyzed amination reaction of various N-heterocyclic chlorides. CrCl2 regioselectively catalyzes the reaction of chloropyridines and dichloropyridines, dichloroquinolines, dichloroisoquinolines and dichloroquinoxalines with a range of aliphatic, allylic, benzylic and saturated (hetero)cyclic magnesium amides in the presence of lithium chloride as additive. The reactions were performed at 50°C in THF and led to the desired aminated products in 56-96% yield.

AB - Abstract We report a ligand-free chromium(II)-catalyzed amination reaction of various N-heterocyclic chlorides. CrCl2 regioselectively catalyzes the reaction of chloropyridines and dichloropyridines, dichloroquinolines, dichloroisoquinolines and dichloroquinoxalines with a range of aliphatic, allylic, benzylic and saturated (hetero)cyclic magnesium amides in the presence of lithium chloride as additive. The reactions were performed at 50°C in THF and led to the desired aminated products in 56-96% yield.

KW - Amination

KW - Chromium

KW - Heterocycles

KW - Magnesium amides

KW - Pyridine

UR - https://www.scopus.com/pages/publications/84939953936

U2 - 10.1055/s-0034-1380178

DO - 10.1055/s-0034-1380178

M3 - Article

AN - SCOPUS:84939953936

SN - 0936-5214

VL - 26

SP - 1049

EP - 1054

JO - Synlett

JF - Synlett

IS - 8

ER -

Chromium(II)-catalyzed amination of N-heterocyclic chlorides with magnesium amides

Abstract

Keywords

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