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Efficient Synthesis and Versatile Reactivity of Porphyrinyl Grignard Reagents
Author(s) -
Fujimoto Keisuke,
Yorimitsu Hideki,
Osuka Atsuhiro
Publication year - 2014
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.201402391
Subject(s) - chemistry , transmetalation , negishi coupling , reactivity (psychology) , reagent , grignard reaction , magnesium , metalation , combinatorial chemistry , organic chemistry , zinc , grignard reagent , medicinal chemistry , catalysis , medicine , alternative medicine , pathology
Iodine–magnesium exchange between iodoporphyrins and i PrMgCl · LiCl proceeded successfully without decomposition of the porphyrin core. The resulting porphyrinyl Grignard reagents are nucleophilic enough to react with various carbonyl compounds, such as aldehydes, ketones, and amides. Furthermore, the porphyrinyl Grignard reagents underwent transmetalation to afford porphyrinyl copper and zinc species of mild and unique reactivity. These could be engaged in 1,4‐addition and Negishi coupling, respectively.