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ISSN 1998-9539

Synthesis of 1,3-Bis(trimethylcyclam) and 1,3-Bis(trimethylcyclen) Substituted Benzenes

Alexei D. Averin,a@ Anton V. Shukhaev,a Alexei K. Buryak,b Franck Denat,c Roger Guilard,c and Irina P. Beletskayaa

aLomonosov Moscow State University, Department of Chemistry, Leninskie Gory, Moscow, 119991 Russia

bA.N. Frumkin Institute of Physical and Electrochemistry, 31 Leninskii prosp., Moscow, 119991, Russia

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

@Corresponding author E-mail: averin@org.chem.msu.ru

Pd-catalyzed amination of 1,3-dibromobenzene with N,N',N''-trimethylcyclam and N,N',N''-trimethylcyclen provided corresponding 1,3-bis(tetraazamacrocyclic) derivatives of benzene in 25-32% yields. The dependence of the products yields on the phosphine ligand applied (BINAP, DavePHOS) as well as on the stoichiometry of starting compounds was established. Scope and limitations for the synthesis of N-phenyl and N-(3-bromophenyl) derivatives of trimethylcyclam and trimethylcyclen were demonstrated.

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