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Direct catalytic arylation of heteroarenes with meso-bromophenyl-substituted porphyrins.

ABSTRACT: The arylation of mono-, di- and tetra-meso-bromophenyl-substituted porphyrins with the heteroarenes containing "acidic" C-H bonds, such as benzoxazole, benzothiazole and N-methylimidazole was studied in the presence of three alternative catalytic systems: Pd(dba)₂/DavePhos/Cs₂CO₃, Pd(PPh₃)₄/PivOH/K₂CO₃ and Pd(OAc)₂/Cu(OAc)₂/PPh₃/K₂CO₃. The first catalytic system was found to be successful in the reaction with benzoxazole, the second one was less efficient for our purpose, while the third system proved to be most versatile and afforded corresponding mono-, di-, tri- and even tetraarylated derivatives of porphyrins.

SUBMITTER: Kiselev AN

PROVIDER: S-EPMC5550796 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Direct catalytic arylation of heteroarenes with meso-bromophenyl-substituted porphyrins.

Kiselev Alexei Nikolaevich AN Grigorova Olga Konstantinovna OK Averin Alexei Dmitrievich AD Syrbu Sergei Aleksandrovich SA Koifman Oskar Iosifovich OI Beletskaya Irina Petrovna IP

Beilstein journal of organic chemistry 20170803

The arylation of mono-, di- and tetra-meso-bromophenyl-substituted porphyrins with the heteroarenes containing "acidic" C-H bonds, such as benzoxazole, benzothiazole and N-methylimidazole was studied in the presence of three alternative catalytic systems: Pd(dba)2/DavePhos/Cs2CO3, Pd(PPh3)4/PivOH/K2CO3 and Pd(OAc)2/Cu(OAc)2/PPh3/K2CO3. The first cataly ...[more]

PMID: 28845197

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