Synthesis of functionalized nitrogen heterocycles from β- and γ-amino acids by radical decarboxylation

Photomediated Controlled Radical Polymerization and Block Copolymerization of Vinylidene Fluoride

“…These trends indicate that all I 2 is rapidly depleted in a fast reaction with the HVICs − , (Scheme , eqs 5 and 5′) to swiftly and quantitatively afford CX 3 COOI. CX 3 COOI could be considered a chain-transfer agent for the polymerization, but its stability under irradiation is quite low, and it is subsequently consumed by photo- ,,− , and by CX 3 • -induced decarboxylation to generate CX 3 I (eqs 4d and 6).…”

“…Because HVICs can alkylate or ligand exchange with many H-labile species, molecular iodine also promotes the hypoiodite reaction ,, of alcohols, ,− , carboxylic acids, ,− and amines. − This constitutes another unusual source of radicals, as the resulting transient R–Y–I − iodinated species photolyzes under UV–vis irradiation to generate the corresponding R–Y • (Y = O, COO, and NH) radicals.…”

Chemistry of Polyvalent Iodine

“…The radical decarboxylation of carboxylic acids on treatment with DIB−I 2 allows us to introduce iodine or other functional groups into nitrogen heterocycles under mild conditions. , For example, the decarboxylation of β- and γ-amino acids 248 under these conditions affords iodinated heterocycles 249 (Scheme ). This reaction was applied to the synthesis of bioactive products, such as opioid analogues, imino sugars, and new antifungal agents …”

“…This reaction was applied to the synthesis of bioactive products, such as opioid analogues, imino sugars, and new antifungal agents. 504 Kita and co-workers developed a simple and reliable method for the direct construction of biologically important aryl lactones 251 from carboxylic acids 250 using a combination of DIB with KBr (Scheme 80). The mechanism of this reaction includes the initial generation of the carbonyloxy radical followed by the intramolecular benzylic hydrogen abstraction and cyclization.…”

Synthesis of Functionalized Nitrogen Heterocycles by Radical Decarboxylation of β‐ and γ‐Amino Acids

“…The formation of halogenated heterocycles following this strategy, and their application to the synthesis of bioactive aza compounds, are discussed herein 9…”