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Most Requested Journal Articles 3Q07-Chemistry and Related Science

Following is one of the journal articles most requested by researchers using CAS electronic products.

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CAS indexed 47 chemical substances from this document. CAS subject entries for this document include: Cycloaddition reaction; Cycloaddition reaction catalysts; Alkynes; and 1 additional concept.

CAPLUS COPYRIGHT 2007 ACS on STN

TITLE:	(NHC)copper(I)-catalyzed [3 + 2] cycloaddition of azides and mono- or disubstituted alkynes
AUTHOR(S):	Diez-Gonzalez, Silvia; Correa, Andrea; Cavallo, Luigi; Nolan, Steven P.
CORPORATE SOURCE:	Institute of Chemical Research of Catalonia, Department of Chemistry, University of New Orleans, New Orleans, LA, 70148, USA
SOURCE:	Chemistry--A European Journal (2006), 12(29), 7558-7564 CODEN: CEUJED; ISSN: 0947-6539
PUBLISHER:	Wiley-VCH Verlag GmbH & Co. KGaA
LANGUAGE:	English

ABSTRACT:
A versatile and highly efficient catalyst for the Huisgen cycloaddn. reaction has been developed. Previously isolated or in situ generated azides yielded 1,2,3-triazoles with differently substituted alkynes in the presence of a [(NHC)CuBr] complex (NHC = N-heterocyclic carbene). Extremely high reaction rates and excellent yields were obtained in all cases. This catalytic system fulfills the requirements of "click chem." with its mild and convenient conditions, notably in water or solvent free reactions and simple isolation with no purifn. step. Furthermore, for the first time, an internal alkyne was successfully used in this copper-catalyzed cycloaddn. reaction. DFT calcns. on this particular system allowed for the proposition of a new mechanistic pathway for disubstituted alkynes.