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Palladium-catalyzed amination in the synthesis of polyazamacrocycles

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Abstract

The review describes palladium-catalyzed amination of acyclic di- and polyamines with aryl halides with a view to reveal general relations holding in this process. Conditions for the synthesis of macrocycles via catalytic diamination of 1,2- and 1,3-dibromobenzenes, 1,3-dichloro-2-bromobenzene, 2,6- and 3,5-dibromopyridines, 3,3′- and 4,4′-dibromobiphenyls, 2,7-dibromonaphthalene, 1,8- and 1,5-dichloroanthracene, 1,8- and 1,5-dichloroanthraquinones, and bis(haloaryl) derivatives of cyclen, cyclam, and cholanediol are discussed. The possibility for palladium-catalyzed arylation of cyclic polyamines has been demonstrated. Specificity of macrocyclization processes and relations between the yield of macrocycles and the nature of initial compounds are considered, and data on the synthesis of cyclic dimers are given. Applications of polyazamacroheterocycles as optical sensors for metal cations are described using as examples macrocyclic compounds derived from 1,8-disubstituted anthraquinone.

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Vorob’evy gory 1, Moscow, 119992, Russia

    I. P. Beletskaya & A. D. Averin

  2. Institut de Chimie Moléculaire de l’Universite de Bourgogne (ICMUB) UMR CNRS 5260, 9 av. Alain Savary, 21078, Dijon, France

    A. G. Bessmertnykh, F. Denat & R. Guilard

Authors
  1. I. P. Beletskaya
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  2. A. D. Averin
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  3. A. G. Bessmertnykh
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  4. F. Denat
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  5. R. Guilard
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Correspondence to I. P. Beletskaya.

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Original Russian Text © I.P. Beletskaya, A.D. Averin, A.G. Bessmertnykh, F. Denat, R. Guilard, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 7, pp. 951–971.

Irina Petrovna Beletskaya. Full Member of the Russian Academy of Sciences, Professor, Head of the Laboratory of Organometallic Compounds, Faculty of Chemistry, Lomonosov Moscow State University. Doctor of chemical sciences since 1963. Fields of scientific interest: chemistry of organometallic compounds, catalysis by transition metal complexes, physical organic chemistry, and chemistry of macrocyclic compounds. I.P. Beletskaya was awarded with numerous prizes, including Demidov’s Prize, Arbuzov’s Prize, and many foreign scientific prizes.

Aleksei Dmitrievich Averin. Leading researcher at the Laboratory of Organometallic Compounds, Faculty of Chemistry, Lomonosov Moscow State University. Candidate of chemical sciences since 1995 (Lomonosov Moscow State University). A.D. Averin worked for several periods at the University of Burgundy. Fields of scientific interest: catalysis by transition metal complexes and chemistry of macrocyclic compounds.

Alla Georgievna Bessmertnykh. Researcher at the LIMRES, University of Burgundy, since 2005. Candidate of chemical sciences since 1988 (Lomonosov Moscow State University). In 2000-2005 she worked in France at the Universities of Toulouse and Reims. Higher degree of research status since 2005. Fields of scientific interest: polyazamacrocyclic compounds, photoactive chemosensors, and materials based thereon.

Frank Denat. Professor at the University of Burgundy. PhD degree since 1993 (Paul Sabatier University of Toulouse, France), works at the University of Burgundy since 1994, Professor since 2005. Fields of scientific interest: synthesis and properties of macrocyclic polyamines and their immobilization on solid supports, design and synthesis of polyfunctional chelating agents for biological and medical research.

Roger Guilard. Professor at the University of Burgundy. PhD degree since 1971. R. Guilard was awarded, among numerous prizes, with Grand Prix of the Academy of Sciences of France in 2001. R. Guilard contributed much to the chemistry of porphyrins, cyclic polyamines, and their complexes with various metals and is editor of the 40-volume porphyrin handbook.

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Beletskaya, I.P., Averin, A.D., Bessmertnykh, A.G. et al. Palladium-catalyzed amination in the synthesis of polyazamacrocycles. Russ J Org Chem 46, 947–967 (2010). https://doi.org/10.1134/S1070428010070018

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