1576-37-0Relevant articles and documents
Synthesis of Amino-Substituted α- And δ-Carbolines via Metal-Free [2 + 2 + 2] Cycloaddition of Functionalized Alkyne-Nitriles with Ynamides
Zhang, Jingyi,Guo, Meichao,Chen, Yajuan,Zhang, Shuangshuang,Wang, Xiao-Na,Chang, Junbiao
, p. 1331 - 1336 (2019)
A metal-free [2 + 2 + 2] cycloaddition of alkyne-cyanamides or ynamide-nitriles with ynamides is described for the efficient synthesis of amino-substituted α- and δ-carbolines. This novel methodology is environmentally friendly and allows for highly regioselective access to carboline derivatives in good to excellent yields with wide functional group tolerance.
Palladium-Catalyzed Oxidative Sulfamidation: A Stereoselective Synthesis for Enesulfonamides
Panda, Niranjan,Yadav, Sushree Arpitabala,Giri, Santanab
, p. 654 - 662 (2017)
A palladium-catalyzed protocol involving oxidative C–H sulfamidation of electron-deficient terminal alkenes is described for the stereoselective synthesis of Z-enesulfonamides. The possible intramolecular hydrogen bonding between the sulfamido proton (SO2N–H) and the carbonyl oxygen (C=O) of the ester group provides extra stability to the resulting alkyl-palladium complex as well as to the transition state. Notably, this reaction operates at room temperature under ligand-free conditions and does not require any inert atmosphere or dry solvent or expensive terminal oxidant. The present protocol enables the stereoselective synthesis of Z-enesulfonamides from the primary sulfonamides and of E-enesulfonamides from N-substituted sulfonamides. Furthermore, the selective deallylation of sulfonamides in the presence of an N-benzyl group was performed under the above reaction conditions. (Figure presented.).
Observation of a Photogenerated Rh2 Nitrenoid Intermediate in C-H Amination
Das, Anuvab,Maher, Andrew G.,Telser, Joshua,Powers, David C.
, p. 10412 - 10415 (2018)
Rh2-catalyzed C-H amination is a powerful method for nitrogenating organic molecules. While Rh2 nitrenoids are often invoked as reactive intermediates in these reactions, the exquisite reactivity and fleeting lifetime of these species has precluded their observation. Here, we report the photogeneration of a transient Rh2 nitrenoid that participates in C-H amination. The developed approach to Rh2 nitrenoids, based on photochemical cleavage of N-Cl bonds in N-chloroamido ligands, has enabled characterization of a reactive Rh2 nitrenoid by mass spectrometry and transient absorption spectroscopy. We anticipate that photogeneration of metal nitrenoids will contribute to the development of C-H amination catalysis by providing tools to directly study the structures of these critical intermediates.
A novel approach for the synthesis of alkyl and aryl sulfonamides
Shaabani, Ahmad,Soleimani, Ebrahim,Hossein Rezayan, Ali
, p. 2185 - 2188 (2007)
A novel approach for the synthesis of alkyl and aryl sulfonamides by the reaction of sulfonic acids, isocyanides and water in dichloromethane is reported at ambient temperature in excellent yields within 20 min. To the best of our knowledge this is the first report on the synthesis of this biologically important family using easily available sulfonic acids and isocyanides.
Heldt
, p. 305,308 (1961)
Selective diethylzinc reduction of imines in the presence of ketones catalyzed by Ni(acac)2
Xiao, Xue,Wang, Haowei,Huang, Zhiyan,Yang, Jun,Bian, Xiaoxia,Qin, Yong
, p. 139 - 142 (2006)
(Chemical Equation Presented) A selective reduction method of an electronically deficient imine in the presence of ketone was developed by employing Et2Zn and 5 mol % of Ni(acac)2. The method was applied in the reduction of SS-tert-butanesulfinyl ketimines 1 to afford amines 2 in 23-92% yields and 73:27 to 98:2 diastereoselectivities. A plausible mechanism was proposed on the basis of an NMR study.
Efficient chiral amidophosphine ligand for copper-catalyzed asymmetric addition of diethylzinc to N-sulfonylimines
Nagai, Kazushige,Fujihara, Hidetaka,Kuriyama, Masami,Yamada, Ken-ichi,Tomioka, Kiyoshi
, p. 8 - 9 (2002)
Structure study of a chiral amidophosphine ligand for copper-catalyzed asymmetric addition reaction of diethylzinc with the N-tosylimine reached to the new chiral phosphine bearing the bulky substituent on the pyrrolidine ring, which significantly improved catalytic performance to give the adduct in 96% yield and 93% ee after 3 h.
Dimethylzinc-mediated alkynylation of imines
Zani, Lorenzo,Alesi, Silvia,Cozzi, Pier Giorgio,Bolm, Carsten
, p. 1558 - 1562 (2006)
The treatment of various aromatic and aliphatic aldimines with a mixture of a terminal alkyne and a commercially available dimethylzinc solution in toluene yields the corresponding protected propargylic amines in moderate to excellent yields. The reaction
Chemoselective Cleavage of Acylsulfonamides and Sulfonamides by Aluminum Halides
Sang, Dayong,Dong, Bingqian,Liu, Yunfeng,Tian, Juan
, p. 3586 - 3595 (2022/02/25)
The chemoselective cleavage of C-N bonds of amides, sulfonamides, and acylsulfonamides by aluminum halides is described. AlCl3and AlI3display complementary reactivities toward N-alkyl and N-acyl moieties. N-Alkylacylsulfonamides, sec
Copper-boryl mediated transfer hydrogenation of N-sulfonyl imines using methanol as the hydrogen donor
He, Yi,Li, Shi-Guang,Mbaezue, Ifenna I.,Reddy, Angula C.S.,Tsantrizos, Youla S.
, (2021/03/24)
B2Pin2-assisted copper-catalyzed transfer hydrogenation of aromatic sulfonylimines has been achieved, delivering a variety of aryl/heteroaryl sulfonamides in good to excellent yields under mild reaction conditions and with methanol a
