Versatile reactivity and catalytic effects of copper(II) halides in organic syntheses

Ferenc Csende, G. Stájer

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Copper(II) salts are widely applied for the halogenation of aromatic and heteroaromatic systems, the hal1737ides. In coupling reactions, CuCl2 has been used as a catalyst for the benzylation of aromates, the synthesis of alkanes, and the preparation of diacetylenes, cyclohexenones and symmetric biaryls. It has further proved suitable for stereoselective cyclization to lactones, carbon-nitrogen coupling and lactamization, and for the simple preparation of aroylaminohydrazones, the allylic amination of olefins, the carbonylation of alkylamines, and heterocyclizations to pyrrolidinones, pyridinones, pyrroles and dihydrofurans. The dehydrogenation of carbocycles and heterocycles can be used in the synthesis of gibberelic acid, for the aromatization of oestrogen derivatives and for the conversion of dihydrouracils to uracils. From tetrahydroisoquinolines, dihydro derivatives have been formed, while dihydropyridazines in the presence of Cu(II) salts yield pyridazines. Similarly, the oxidations of cyclohexane, adamantane and methylcatechol to benzoquinone, and amines to nitriles have been performed. The conversion of aldehydes to nitriles and benzyl radical cyclizations to butyrolactones have been achieved. Protection and deprotection, and various other Cu(II) halide-mediated reactions are also discussed.

Original languageEnglish
Pages (from-to)1737-1755
Number of pages19
JournalCurrent Organic Chemistry
Volume9
Issue number17
DOIs
Publication statusPublished - Nov 2005

Fingerprint

Nitriles
Cyclization
Copper
Pyridazines
Salts
Halogenation
Adamantane
Tetrahydroisoquinolines
Pyridones
Derivatives
Pyrrolidinones
Carbonylation
Aromatization
Amination
Pyrroles
Alkanes
Uracil
Alkenes
Lactones
Dehydrogenation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Versatile reactivity and catalytic effects of copper(II) halides in organic syntheses. / Csende, Ferenc; Stájer, G.

In: Current Organic Chemistry, Vol. 9, No. 17, 11.2005, p. 1737-1755.

Research output: Contribution to journalArticle

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