948-15-2Relevant academic research and scientific papers
Double acylation of alkenes with acylchromates promoted by cationic Pd(II) complex
Yamane, Motoki,Ishibashi, Yuichiro,Sakurai, Hidehiro,Narasaka, Koichi
, p. 174 - 175 (2000)
Double acylation of alkenes such as norbornene and vinyl-silane proceeds by the use of acylchromate complexes and a cationic Pd(II) complex. When two different acylchromates are added successively to a mixture of alkene and the Pd complex, unsymmetrical diketones are obtained almost selectively.
Synergistic Activation of Amides and Hydrocarbons for Direct C(sp3)–H Acylation Enabled by Metallaphotoredox Catalysis
Baik, Mu-Hyun,Choi, Seulhui,Hong, Soon Hyeok,Lee, Geun Seok,Won, Joonghee
, p. 16933 - 16942 (2020/08/03)
The utilizations of omnipresent, thermodynamically stable amides and aliphatic C(sp3)?H bonds for various functionalizations are ongoing challenges in catalysis. In particular, the direct coupling between the two functional groups has not been realized. Here, we report the synergistic activation of the two challenging bonds, the amide C?N and unactivated aliphatic C(sp3)?H, via metallaphotoredox catalysis to directly acylate aliphatic C?H bonds utilizing amides as stable and readily accessible acyl surrogates. N-acylsuccinimides served as efficient acyl reagents for the streamlined synthesis of synthetically useful ketones from simple C(sp3)?H substrates. Detailed mechanistic investigations using both computational and experimental mechanistic studies were performed to construct a detailed and complete catalytic cycle. The origin of the superior reactivity of the N-acylsuccinimides over other more reactive acyl sources such as acyl chlorides was found to be an uncommon reaction pathway which commences with C?H activation prior to oxidative addition of the acyl substrate.
Palladium-catalyzed formal hydroacylation of allenes employing acid chlorides and hydrosilanes
Fujihara, Tetsuaki,Tatsumi, Kenta,Terao, Jun,Tsuji, Yasushi
supporting information, p. 2286 - 2289 (2013/06/05)
The palladium-catalyzed formal hydroacylation of allenes employing acid chlorides and hydrosilanes has been achieved. The reactions proceed with commercially available Pd(OAc)2 as a catalyst and HSi(iPr) 3 as a reducing reagent, giving the corresponding α,β-unsaturated ketones regio- and stereoselectively.
