Premium
Facile, One‐Pot, and Gram‐Scale Synthesis of 3,4,5‐Triiodoanisole through a C–H Iodination/ ipso ‐Iododecarboxylation Strategy: Potential Application towards 3,4,5‐Trisubstituted Anisoles
Author(s) -
AlZoubi Raed M.,
AlMughaid Hussein,
AlZoubi Mariam A.,
Jaradat Khaled T.,
McDonald Robert
Publication year - 2015
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.201500887
Subject(s) - chemistry , halogenation , yield (engineering) , anisole , regioselectivity , catalysis , combinatorial chemistry , organic chemistry , benzoic acid , iodine , materials science , metallurgy
A facile, efficient, and gram‐scale method for the conversion of para ‐anisic acid into 3,4,5‐triiodoanisole through a one‐pot C–H iodination/ ipso ‐iododecarboxylation reaction was investigated. Commercially available benzoic acid was used, which allowed the reaction to be performed on a multigram scale in good yield. This report discloses a practical method for the one‐pot synthesis of hitherto unknown 3,4,5‐triiodoanisole that is catalytic, scalable, efficient, and easy to work up and purify. Potential application of the target compound as a precursor for novel site‐selective metal–iodine exchange and Suzuki–Miyaura cross‐coupling reactions were also explored. 3,4,5‐Trisubstituted anisole derivatives were provided in a highly regioselective fashion; these compounds are useful building blocks in synthesis and indeed are hard to prepare by any other means.