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Synthesis of Diiodinated Biphenyls and Iodinated meta ‐Terphenyls by Regioselective Suzuki–Miyaura Cross‐Coupling Reactions of 5‐Substituted 1,2,3‐Triiodobenzenes
Author(s) -
AlZoubi Raed M.,
AlJammal Walid K.,
ElKhateeb Mohammad Y.,
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.201500263
Subject(s) - regioselectivity , chemistry , biphenyl , steric effects , coupling reaction , combinatorial chemistry , terphenyl , organic chemistry , medicinal chemistry , catalysis
A variety of 2,3‐diiodinated biphenyl and iodinated meta ‐terphenyl derivatives were synthesized by a regioselective Suzuki–Miyaura cross‐coupling reaction of 5‐substituted 1,2,3‐triiodobenzenes. By using 1 equiv. of arylboronic acid, the Suzuki–Miyaura reaction yielded 2,3‐diiodinated biphenyl derivatives with excellent regioselectivity. The coupling reaction predominantly occurred at the terminal position of the 5‐substituted 1,2,3‐triiodobenzene, which is the less sterically hindered and more electronically deficient site. With 2 equiv. of arylboronic acids, the one‐pot reaction provided iodinated meta ‐terphenyls in good yields. This facile and efficient one‐step method is also quite general in scope as well as scalable.