Iridium(III)-Catalyzed Intermolecular C(sp3)-H Insertion Reaction of Quinoid Carbene: A Radical Mechanism was written by Wang, Hai-Xu;Richard, Yann;Wan, Qingyun;Zhou, Cong-Ying;Che, Chi-Ming. And the article was included in Angewandte Chemie, International Edition in 2020.Formula: C10H17NO2 This article mentions the following:
In the presence of (octaethylporphyrinato)methyliridium, diazocyclohexadienones such as I underwent regioselective C-H insertion reactions with cyclohexadienes, alkenes, indene, THF, and Boc-pyrrolidine to yield dihydrobiaryls such as II and alkenylarenes and alkylarenes. TEMPO inhibition experiments, kinetic isotope effects, identification of an iridium carbene intermediate, and calculated structure and spin d. for an iridium carbene-derived radical provided evidence for a radical reaction mechanism for the insertion reactions; the insertions are proposed to occur by hydrogen atom transfer to the iridium carbene followed by radical rebound. The regioselectivity of the insertion reactions are determined primarily by steric effects, with insertion into primary C-H bonds favored over insertion into secondary or tertiary C-H bonds. In the experiment, the researchers used many compounds, for example, tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4Formula: C10H17NO2).
tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Formula: C10H17NO2