1099591-96-4Relevant academic research and scientific papers
Complete Switch of Selectivity in the C-H Alkenylation and Hydroarylation Catalyzed by Iridium: The Role of Directing Groups
Kim, Jiyu,Park, Sung-Woo,Baik, Mu-Hyun,Chang, Sukbok
supporting information, p. 13448 - 13451 (2015/11/09)
A complete switch in the CpIr(III)-catalyzed paths between C-H olefination and hydroarylation was found to be crucially dependent on the type of directing groups. This dichotomy in product distribution was correlated to the efficiency in attaining syn-coplanarity of olefin-inserted 7-membered iridacycles. Theoretical studies support our hypothesis that the degree of flexibility of this key intermediate modulates the β-H elimination, which ultimately affords the observed chemoselectivity.
Mild palladium-catalyzed C-H alkylation using potassium alkyltrifluoroborates in combination with MnF3
Neufeldt, Sharon R.,Seigerman, Cydney K.,Sanford, Melanie S.
supporting information, p. 2302 - 2305 (2013/06/05)
A Pd-catalyzed method for ligand-directed C-H alkylation with organoboron reagents is described. The combination of potassium organotrifluoroborates, MnF3, and a PdII catalyst effects pyridine and amide-directed C-H alkylation. These reactions proceed under mild conditions (25-40 C in weakly acidic media), are effective for installing methyl and 1 alkyl groups, and do not require promoters such as benzoquinone.
Reactions and mechanistic studies of rhenium-catalyzed insertion of α,β-unsaturated carbonyl compounds into a C-H bond
Kuninobu, Yoichiro,Nishina, Yuta,Okaguchi, Kayo,Shouho, Makoto,Takai, Kazuhiko
experimental part, p. 1393 - 1401 (2009/05/06)
A rhenium complex, [ReBr(CO)3(thf)]2, catalyzes the insertion of α, β-unsaturated carbonyl compounds into a C-H bond of aromatic compounds having nitrogen-containing directing groups. In this reaction, Re2(CO)10 can also be used as a catalyst. When imines are employed as the aromatic substrates, sequential cyclization proceeds and indene derivatives are obtained in good to excellent yields. This reactivity is in contrast to those of ruthenium and rhodium complexes, which are usually used as catalysts in the insertion reactions of unsaturated molecules into a C-H bond. Investigations on the reaction mechanism indicate that the rhenium catalyst promotes C-H bond activation of aromatic compounds, the insertion of α, β-unsaturated carbonyl compounds into a Re-C bond, and intramolecular nucleophilic cyclization followed by reductive elimination and the elimination of an amine.
