6942-75-2Relevant academic research and scientific papers
Radical C(sp2)-H Trifluoromethylation of Aldehydes in Aqueous Solution
Zhang, Pei,Shen, Haigen,Zhu, Lin,Cao, Weiguo,Li, Chaozhong
supporting information, p. 7062 - 7065 (2018/11/21)
The copper-mediated C(sp2)-H trifluoromethylation of aldehydes is described. The reaction of aldehydes with (bpy)Cu(CF3)3, Et3SiH, and K2S2O8 in aqueous acetone at room temperatu
Scalable, Electrochemical Oxidation of Unactivated C-H Bonds
Kawamata, Yu,Yan, Ming,Liu, Zhiqing,Bao, Deng-Hui,Chen, Jinshan,Starr, Jeremy T.,Baran, Phil S.
supporting information, p. 7448 - 7451 (2017/06/13)
A practical electrochemical oxidation of unactivated C-H bonds is presented. This reaction utilizes a simple redox mediator, quinuclidine, with inexpensive carbon and nickel electrodes to selectively functionalize "deep-seated" methylene and methine moieties. The process exhibits a broad scope and good functional group compatibility. The scalability, as illustrated by a 50 g scale oxidation of sclareolide, bodes well for immediate and widespread adoption.
The first general and selective palladium(II)-catalyzed alkoxycarbonylation of arylboronates: Interplay among benzoquinone-ligated palladium(0) complex, organoboron, and alcohol solvent
Yamamoto, Yoshihiko
supporting information; experimental part, p. 478 - 492 (2010/07/03)
Methoxycarbonylation of aryl- and alken-ylboron compounds was performed using the palladium (II) acetate/triphenylphosphine [PdACHTUNGTRENNUNG(OAc) 2/PPh3] catalyst with p-benzoquinone as a stoichiometric oxidant in methanol at ambient temperature to obtain the corresponding methyl esters in good yields. A wide variety of functional groups including various carbonyl functionalities, nitrile, nitro, sulfone, and unprotected pyrrole rings were tolerated in the methoxycarbonlation, while the use of higher alcohols except for tert-butanol afforded various pchlorobenzoates in moderate to high yields. The catalytic alkoxycarbonylation proceeded without any acid or base additive, and an oxidative transmetalation step is proposed to explain the exceptional efficacy of this protocol. DFT and MP2 calculations support the proposed mechanism.
