143287-98-3Relevant academic research and scientific papers
Ni-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Thiocarbonates via C-O/C-O Bond Cleavage
Zhu, Zhaodong,Gong, Yuxin,Tong, Weiqi,Xue, Weichao,Gong, Hegui
supporting information, p. 2158 - 2163 (2021/04/05)
A nickel-catalyzed reductive coupling of aryl triflates with thiocarbonates is reported here. Both electron-rich and -deficient aryl C(sp2)-O electrophiles as well as a class of O-tBu S-alkyl thiocarbonates are compatible with the optimized reaction conditions, as evidenced by 49 examples. The reaction also proceeds with good chemoselective cleavage of the C-O bond with regard to thioesters. This work broadens the scope of nickel-catalyzed reductive cross-electrophile coupling reactions.
Pd-Catalyzed Difluoromethylthiolation of Aryl Chlorides, Bromides and Triflates
Wu, Jiang,Lu, Changhui,Lu, Long,Shen, Qilong
supporting information, p. 1031 - 1034 (2018/09/25)
A highly efficient Pd-catalyzed difluoromethylthiolation of aryl chlorides, bromides and triflates is described. A variety of aryl halides with common functional groups were difluoromethylthiolated in moderate to excellent yields. Furthermore, several nat
Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents
Edelstein, Emma K.,Namirembe, Sheila,Morken, James P.
supporting information, p. 5027 - 5030 (2017/05/04)
Palladium-catalyzed conjunctive cross-coupling is used for the synthesis of enantioenriched allylboron reagents. This reaction employs nonsymmetric bis(alkenyl)borates as substrates and appears to occur by a mechanism that involves selective activation of the less substituted alkene followed by migration of the more substituted alkene during the course of a Pd-induced metalate rearrangement.
Palladium on carbon-diethylamine-mediated hydrodeoxygenation of phenol derivatives under mild conditions
Mori, Akinori,Mizusaki, Tomoteru,Ikawa, Takashi,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
, p. 1270 - 1280 (2007/10/03)
We have found that phenolic hydroxyl groups were readily deoxygenated via aryl sulfonate under the Pd/C-catalyzed hydrogenation conditions in the presence of diethylamine and the method could also be applicable to the hydrodeoxygenation of morphine to afford 3-deoxy-7,8-dihydromorphine. Diethylamine is not only a scavenger of the corresponding methanesulfonic acid derivative, which is produced during the reaction progress, but also a strong promoter of the Pd/C-catalyzed reduction of aryl sulfonates. This catalyst system could provide a general method for the deoxygenation of various phenol derivatives because of its mild reaction conditions, ease of handling, and no need of particular apparatus.
Mechanistic study of a Pd/C-catalyzed reduction of aryl sulfonates using the Mg-MeOH-NH4OAc system
Mori, Akinori,Mizusaki, Tomoteru,Ikawa, Takashi,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
, p. 1432 - 1441 (2008/02/04)
A method for the deoxygenation of phenolic hydroxy groups via aryl triflates or mesylates has been established by using a combination of Pd/ C-Mg-MeOH. The addition of NH4OAc to the system markedly accelerated the reaction rate and expanded the scope of the reaction. Mechanistic studies suggested that a single-electron transfer process from the Pd0 center to the benzene ring is involved in the reduction of aryl sulfonates and that NH4OAc works as a solubilization re agent of the Mg salt and as an accelerator of the electron transfer, thus enhancing the reaction process. Our method was also applicable to the regioselective deuteration of benzene derivatives with CH3OD as the solvent and deuterium source: the original hydroxy group could be efficiently replaced with a deuterium atom.
Pd/C-catalyzed deoxygenation of phenol derivatives using mg metal and MeOH in the presence of NH4OAc
Sajiki, Hironao,Mori, Akinori,Mizusaki, Tomoteru,Ikawa, Takashi,Maegawa, Tomohiro,Hirota, Kosaku
, p. 987 - 990 (2007/10/03)
A Pd/C-catalyzed deoxygenation method of phenolic hydroxyl groups via aryl triflates or mesylates using Mg metal in MeOH at room temperature was developed. The addition of NH4OAc dramatically affects the reactivity and reaction rate. This method is particularly attractive to provide an environmentally benign and widely applicable removal method of phenolic alcohols under quite mild reaction conditions.
Rapid synthesis of acyl transfer auxiliaries for cysteine-free native glycopeptide ligation
Macmillan, Derek,Anderson, David W.
, p. 4659 - 4662 (2007/10/03)
(Chemical Equation Presented) Rapid, facile routes to the TFA-cleavable 4,5,6-trimethoxy-2-mercaptobenzyl and 1-(2,4-dimethoxyphenyl)-2-mercaptoethyl classes of auxiliaries for cysteine-free native chemical ligation are described. Rapid synthesis, coupled
