58173-67-4Relevant articles and documents
Design and implementation of a catalytic electron donor?acceptor complex platform for radical trifluoromethylation and alkylation
Stephenson, Corey R.J.,McClain, Edward J.,Monos, Timothy M.,Mori, Mayuko,Beatty, Joel W.
, p. 12636 - 12641 (2020/11/18)
Electron donor?acceptor (EDA) complexes can controllably generate radicals under mild conditions through selective photoexcitation events. However, unproductive reactivity from fast deactivation of the photoexcited complexes through back electron transfer has slowed the development of EDA complexes in synthetic methodology. Here, we disclose the study of EDA complexes derived from 2-methoxynaphthalene donor and acylated ethyl isonicotinate N-oxide acceptor that undergo a fast N?O bond fragmentation event upon photoexcitation. This reaction design not only overcomes the limitations of back electron transfer but also enables regeneration of the donor species, representing a rare example of EDA photochemistry in a catalytic regime. The synthetic utility is demonstrated through visible light-driven radical trifluoromethylation and Minisci alkylation reactions. The scalability of the EDA complex-promoted reaction is evidenced by the successful multigram-scale trifluoromethylation of methyl N-Boc pyrrole-2-carboxylate in a continuous flow manifold.
Palladium-catalyzed cross-coupling reaction of trialkylbismuthines with 2-haloazines and diazines
Petiot, Pauline,Gagnon, Alexandre
, p. 1615 - 1624 (2016/10/12)
An efficient method for the cross-coupling reaction of primary trialkybismuth reagents with 2-haloazines and diazines is reported. The reaction functions with pyridines, pyrimidines, pyridazines and pyrazines and tolerates many functional groups. This method gives access to 2-alkylazines and diazines, a class of compounds which is important in medicinal chemistry.
Cross-coupling of cyclopropyl- and cyclobutyltrifluoroborates with aryl and heteroaryl chlorides
Molander, Gary A.,Gormisky, Paul E.
, p. 7481 - 7485 (2008/12/23)
(Chemical Equation Presented) Suitable conditions were found for the Suzuki-Miyaura cross-coupling reaction of potassium cyclopropyl-and cyclobutyltrifluoroborates with aryl chlorides. Both of these secondary alkyl trifluoroborates coupled in moderate to excellent yield with electron-rich, electron-poor, and hindered aryl chlorides to give a variety of substituted aryl cyclopropanes and cyclobutanes.
