92433-38-0Relevant academic research and scientific papers
Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts
Liu, Long,Tang, Yuanyuan,Wang, Kunyu,Huang, Tianzeng,Chen, Tieqiao
, p. 4159 - 4170 (2021/03/09)
A facile and general method for constructing carbon-heteroatom (C-P, C-O, C-S, and C-N) bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.
A Catalytic One-Pot Synthesis of Indolyl Cyclobutanones
Porcu, Stefania,Rodriguez, Carla Aira,Frongia, Angelo,Secci, Francesco
supporting information, p. 925 - 932 (2020/12/14)
A general strategy for the synthesis of indolyl cyclobutanones via a tandem Bronsted acid catalyzed 2-hydroxycyclobutanone activation-indole nucleophilic addition has been exploited. The procedure leads to a wide range of 2- and 3-functionalized indole derivatives in good to high yields with broad substrate scope.
The palladium-catalyzed direct C3-cyanation of indoles using acetonitrile as the cyanide source
Feng, Kejun,Li, Qiang,Li, Yuanhua,Liu, Bifu,Liu, Min,Zhou, Yongbo
supporting information, p. 6108 - 6114 (2020/10/21)
The ligand-free palladium-catalyzed C3-cyanation of indoles via direct C-H functionalization was achieved. This protocol, utilizing CH3CN as a green and readily available cyanide source, produced the desired products in moderate to good yields through transition-metal-catalyzed C-CN bond cleavage. This journal is
Efficient acceptorless photo-dehydrogenation of alcohols and: N -heterocycles with binuclear platinum(ii) diphosphite complexes
Zhong, Jian-Ji,To, Wai-Pong,Liu, Yungen,Lu, Wei,Che, Chi-Ming
, p. 4883 - 4889 (2019/05/16)
Although photoredox catalysis employing Ru(ii) and Ir(iii) complexes as photocatalysts has emerged as a versatile tool for oxidative C-H functionalization under mild conditions, the need for additional reagents acting as electron donor/scavenger for completing the catalytic cycle undermines the practicability of this approach. Herein we demonstrate that photo-induced oxidative C-H functionalization can be catalysed with high product yields under oxygen-free and acceptorless conditions via inner-sphere atom abstraction by binuclear platinum(ii) diphosphite complexes. Both alcohols (51 examples), particularly the aliphatic ones, and saturated N-heterocycles (24 examples) can be efficiently dehydrogenated under light irradiation at room temperature. Regeneration of the photocatalyst by means of reductive elimination of dihydrogen from the in situ formed platinum(iii)-hydride species represents an alternative paradigm to the current approach in photoredox catalysis.
Design and synthesis of multipotent 3-aminomethylindoles and 7-azaindoles with enhanced protein phosphatase 2A-activating profile and neuroprotection
Lajarín-Cuesta, Rocío,Arribas, Raquel L.,Nanclares, Carmen,García-Frutos, Eva M.,Gandía, Luis,de los Ríos, Cristóbal
, p. 294 - 309 (2018/08/17)
We report the synthesis and pharmacological evaluation of new 3-aminomethylindoles derivatives with neuroprotective properties designed to present multi-target activity centered on reducing the neuronal Ca2+ overload and preventing phosphatase
General and efficient synthesis of 2,3-unsubstituted indoles catalyzed by acidic mesoporous molecular sieves
Sun, Nan,Hong, Lingfen,Huang, Fang,Ren, Hong,Mo, Weimin,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
, p. 3927 - 3933 (2013/06/27)
A general and efficient method for the synthesis of 2,3-unsubstituted indoles has been established by the intramolecular cyclization of N-benzyl 2-anilinoacetals. Acidic mesoporous molecular sieve (MCM-41-SO3H) has shown excellent catalytic activity on this transformation, and the 2,3-unsubstituted indoles bearing 7-substituent or strong electron-withdrawing substituents also could be achieved by this protocol. Moreover, the heterogeneous catalyst, MCM-41-SO3H, could be conveniently recovered and reused without obvious loss of the catalytic activity. This work will provide an economic and environmental-benign method for the construction of various indole derivatives.
On water phosphine-free palladium-catalyzed room temperature C-H arylation of indoles
Islam, Saidul,Larrosa, Igor
supporting information, p. 15093 - 15096 (2013/11/06)
Get on top of your chemistry! An "on water", palladium-catalyzed, phosphine-free direct C-H arylation of indoles, with iodoarenes at 25-30°C, is disclosed (see scheme; TBDMS=N-tert-butyldimethylsilyl ether; SEM=N-2-(trimethylsilyl)ethoxymethyl; Bn=benzyl, Piv=pivabyl). The mildness of the reaction conditions permits the tolerance of a variety of N1-protected indoles.
Copper-catalysed direct C-H bond oxidative acetoxylation and iodination of indoles
Ge, Shao-Peng,Zhang, Xiao-Hong,Han, Jiang-Sheng,Zhong, Ping
experimental part, p. 356 - 359 (2012/10/08)
A novel Cu(OAc)2-catalysed direct C-H bond oxidative acetoxylation and iodination of indoles using PhI(OAc)2 as a terminal oxidant is reported. Adopting this method, a series of 3-iodoindoles and indol-3-yl acetates were obtained in nearly 1:1 ratio yield.
Iodonium salts are key intermediates in Pd-catalyzed acetoxylation of pyrroles
Lubriks, Dmitrijs,Sokolovs, Igors,Suna, Edgars
supporting information; experimental part, p. 4324 - 4327 (2011/10/05)
A mild, room-temperature Pd-catalyzed acetoxylation of pyrroles with phenyliodonium acetate is described. The acetoxylation was found to proceed via the initial formation of pyrrolyl(phenyl)iodonium acetates, which were converted to acetoxypyrroles in the presence of Pd(OAc)2. The acetoxylation could also be carried out as a one-pot sequential procedure without the isolation of the intermediate iodonium salts.
Synthesis of indole and biindolyl triflones: Trifluoromethanesulfonylation of indoles with Tf2O/TTBP (2,4,6-tri- tert -butylpyridine) system
Xu, Xiu-Hua,Liu, Guo-Kai,Azuma, Ayaka,Tokunaga, Etsuko,Shibata, Norio
supporting information; experimental part, p. 4854 - 4857 (2011/11/06)
A convenient synthesis of indole triflones is reported. N-Alkyl, aryl and N-H indole triflones were obtained in 82-96% yields by the Tf2O/TTBP System. Biindolyl triflones were accessed in 51-81% yields for the first time by simple treatment of the resulting indole triflones with a base and without any use of organometallic chemistry. An environmentally friendly solvent, Solkane 365/227, can be substituted for this process without any loss of efficiency.
