520-03-6Relevant articles and documents
Defined Palladium-Phthalimidato Catalysts for Improved Oxidative Amination
Martínez, Claudio,Mu?iz, Kilian
, p. 7367 - 7370 (2016)
New palladium(II)-phthalimidato complexes have been synthesized, isolated, and structurally characterized. As demonstrated from over 30 examples, they constitute superior catalysts for oxidative amination reactions of alkenes with phthalimide as the nitrogen source. This work streamlines vicinal difunctionalization of alkenes and provides access to significantly improved and experimentally simplified synthetic protocols.
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Rogow
, p. 1796 (1897)
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Photoinduced reactions of 1,3,4(2H)-isoquinolinetriones with diphenylacetylenes - An efficient one pot syntheses of dibenz[de,g]-(2H)-isoquinoline-4, 6-dione derivatives
Zhang,Qian,Fun,Xu
, p. 8141 - 8145 (2000)
Photoinduced reactions of 1,3,4(2H)-isoquinolinetriones with diphenylacetylenes afforded the corresponding dibenz[de,g]-(2H)-isoquinoline-4,6-dione derivatives in moderate to high yields via a reaction sequence involving [2+2] photocycloaddition, ring opening rearrangement of the oxetene intermediate and dehydrogenative cyclization in one pot. (C) 2000 Elsevier Science Ltd.
Mechanistic Studies of Ullmann-Type C–N Coupling Reactions: Carbonate-Ligated Copper(III) Intermediates
Gurjar, Kamlesh K.,Sharma, Rajendra K.
, p. 862 - 869 (2017)
In Ullmann-type C?N coupling reactions, the involvement of CuIII species has been proposed many times on the basis of the oxidative addition–reductive elimination (OA-RE) path for these reactions, but actual species could not be traced in experimental studies. In the C?N coupling reactions, carbonate and phosphate were considered widely as bases. In the present study, Cu-mediated C?N coupling reactions of aryl halides and NuNH (amide and imide) were investigated extensively, and we provide direct spectroscopic evidence of actual CuIII species. For the first time, we reveal that carbonate and phosphate ions act as bidentate ligands as well as a base in the catalytic cycle, and thus the actual intermediate species is a carbonate- or phosphate-ligated, distorted octahedral CuIII complex. Our experimental and computational studies have strengthened the hypothesis that these reactions follow an OA-RE path.
Solvent-free, Efficient Transamidation of Carboxamides with Amines Catalyzed by Recyclable Sulfated Polyborate Catalyst
Mali, Anil S.,Indalkar, Krishna,Chaturbhuj, Ganesh U.
, p. 369 - 378 (2021/07/26)
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Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams
Bai, Ya,Shi, Lingling,Zheng, Lianyou,Ning, Shulin,Che, Xin,Zhang, Zhuoqi,Xiang, Jinbao
supporting information, p. 2298 - 2302 (2021/04/05)
An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr2NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity.
“On water” nano-Cu2O-catalyzed CO-free one-pot multicomponent cascade cyanation-annulation-aminolysis reaction toward phthalimides
Wen, Xiaowei,Liu, Xiaojuan,Yang, Zhiqi,Xie, Menglan,Liu, Yuxi,Long, Lipeng,Chen, Zhengwang
supporting information, p. 1738 - 1743 (2021/03/14)
An efficient nano-Cu2O-catalyzed cascade multicomponent reaction of 2-halobenzoic acids and trimethylsilyl cyanide with diverse amines was developed using water as a solvent, affording versatileN-substituted phthalimide derivatives in moderate to excellent yields. This novel strategy features carbon monoxide gas-free, environmentally benign, one-pot multistep transformation, commercially available reagents, a cheap catalyst without any additives, wide functional group tolerance, and operational convenience.