39695-18-6Relevant articles and documents
Defunctionalization of sp3 C–Heteroatom and sp3 C–C Bonds Enabled by Photoexcited Triplet Ketone Catalysts
An, Juzeng,Gu, Yiting,Martin, Ruben,Wakeling, Matthew,Yin, Hongfei
, p. 1031 - 1036 (2022/01/19)
A general strategy for enabling a light-induced defunctionalization of sp3 C–heteroatom and sp3 C–C bonds with triplet ketone catalysts and bipyridine additives is disclosed. This protocol is characterized by its broad scope without recourse to transition metal catalysts or stoichiometric exogeneous reductants, thus offering a complementary technique for activating σ sp3 C–C(heteroatom) bonds. Preliminary mechanistic studies suggest that the presence of 2,2′-bipyridines improves the lifetime of ketyl radical intermediates.
Catalytic reductive deoxygenation of esters to ethers driven by hydrosilane activation through non-covalent interactions with a fluorinated borate salt
Agbossou-Niedercorn, Francine,Dixit, Ruchi,Merle, Nicolas,Michon, Christophe,Rysak, Vincent,Trivelli, Xavier,Vanka, Kumar
, p. 4586 - 4592 (2020/08/14)
We report the catalytic and transition metal-free reductive deoxygenation of esters to ethers through the use of a hydrosilane and a fluorinated borate BArF salt as a catalyst. Experimental and theoretical studies support the role of noncovalent interactions between the fluorinated catalyst, the hydrosilane and the ester substrate in the reaction mechanism.
Palladium on Carbon-Catalyzed Benzylic Methoxylation for Synthesis of Mixed Acetals and Orthoesters
Yasukawa, Naoki,Kanie, Takafumi,Kuwata, Marina,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 10974 - 10977 (2017/08/22)
The palladium on carbon (Pd/C)-catalyzed direct methoxylation of the benzylic positions of linear benzyl and cyclic ether substrates proceeded in the presence of i-Pr2NEt under an oxygen atmosphere to give the corresponding mixed acetals. Cyclic acetal derivatives could also be converted into orthoesters. The present direct methoxylation via a carbon-hydrogen (C?H) functionalization can be accomplished using the easily-removed Pd/C and molecular oxygen as a green oxidant. The obtained mixed acetals were transformed into the corresponding ether products by chemoselective substitution of the methoxy group using a silyltriflate, 2,4,6-collidine, and a nucleophile. The orthoester derivative could also be transformed into the cyclic ketal under similar reaction conditions.
Visible-light-promoted conversion of alkyl benzyl ether to alkyl ester or alcohol via O-α-sp3 C-H cleavage
Lu, Ping,Hou, Tianyuan,Gu, Xiangyong,Li, Pixu
supporting information, p. 1954 - 1957 (2015/04/27)
A mild and high-yielding visible-light-promoted conversion of alkyl benzyl ethers to the alkyl esters or alkyl alcohols was developed. Mechanistic studies provided evidence for a radical chain reaction involving the homolytic cleavage of O-α-sp3 C-H bonds in the substrate as one of the propagation steps. We propose that α-bromoethers are key intermediates in the transformation.
[IrCl2Cp*(NHC)] complexes as highly versatile efficient catalysts for the cross-coupling of alcohols and amines
Prades, Amparo,Corberan, Rosa,Poyatos, Macarena,Peris, Eduardo
scheme or table, p. 11474 - 11479 (2009/12/03)
A comparative study on the catalytic activity of a series of [IrCl 2Cp*(NHC)] complexes in several C-O and C-N coupling processes implying hydrogen-borrowing mechanisms has been performed. The compound [IrCl2Cp*(InBu)] (Cp* = pentamethyl cyclopentadiene; InBu = 1,3-di-n-butylimidazolylidene) showed to be highly effective in the cross-coupling reactions of amines and alcohols, providing high yields in the production of unsymmetrical ethers and N-alkylated amines. A remarkable feature is that the processes were carried out in the absence of base, phosphine, or any other external additive. A comparative study with other known catalysts, such as Shvo's catalyst, is also reported.
A Novel Method for the Preparation of Ethers from Carbonyl Compounds with Benzenetellurol Catalyzed by ZnI2
Nagakawa, Keiichi,Osuka, Masahiro,Sasaki, Kazuaki,Aso, Yoshio,Otsubo, Tetsuo,Ogura, Fumio
, p. 1331 - 1334 (2007/10/02)
Benzenetellurol is shown to behave as an effective reagent for the reductive conversion of carbonyl compounds into unsymmetrical ethers under the catalytic influence of ZnI2.
