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Regioselective Carbon‐Halogen Bond Formation in the Reaction of Ag(III) N ‐Confused Porphyrin Complex with HCl or HBr
Author(s) -
Sumra Idrees,
Irfan Majeed,
He Huowang,
Zhang Yihuan,
Hao Fei,
Lin Jinhong,
Osuka Atsuhiro,
Zeng Zhuo,
Jiang HuaWei
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100777
Subject(s) - chemistry , halogenation , regioselectivity , halogen , porphyrin , yield (engineering) , halide , medicinal chemistry , alkoxy group , photochemistry , organic chemistry , alkyl , catalysis , materials science , metallurgy
A facile inner halogenation of Ag(III) NCP complex 1 is reported. Treatment of 1 with 2 N HCl and 1 N HBr gave 2 and 4 , respectively. A demetallized product 3 was formed as a trace side product when dilute acids were applied and as a predominant product when treated with concentrated acids. The importance of the C3‐ethoxy group for the halogenation reactions was experimentally indicated. Treatment of 1 with 4 N H 2 SO 4 gave carbaporpholactam 6 in good yield. Halide anions are suggested to accelerate the demetallation reaction of 1 .