6533b7d5fe1ef96bd1264963
RESEARCH PRODUCT
Synthesis of 1,3-bis(trimethylcyclam) and 1,3-bis(trimethylcyclen) substituted benzenes
Anton V. ShukhaevAlexei D. AverinIrina P. BeletskayaAlexei K. BuryakFranck DenatRoger Guilardsubject
010405 organic chemistryLigandPd catalysis[CHIM.ORGA]Chemical Sciences/Organic chemistryOrganic Chemistryamination[CHIM.ORGA] Chemical Sciences/Organic chemistry010402 general chemistry01 natural sciences0104 chemical sciencesAnalytical Chemistryaryl halideschemistry.chemical_compoundchemistrytetraazamacrocycles[ CHIM.ORGA ] Chemical Sciences/Organic chemistryOrganic chemistryBenzenePhosphineStoichiometryAminationComputingMilieux_MISCELLANEOUSBINAPdescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2009-01-01 |