26060-56-0Relevant academic research and scientific papers
Synthesis of Sterically Hindered Primary Amines by Concurrent Tandem Photoredox Catalysis
Nicastri, Michael C.,Lehnherr, Dan,Lam, Yu-Hong,Dirocco, Daniel A.,Rovis, Tomislav
supporting information, p. 987 - 998 (2020/01/31)
Primary amines are an important structural motif in active pharmaceutical ingredients (APIs) and intermediates thereof, as well as members of ligand libraries for either biological or catalytic applications. Many chemical methodologies exist for amine synthesis, but the direct synthesis of primary amines with a fully substituted α carbon center is an underdeveloped area. We report a method which utilizes photoredox catalysis to couple readily available O-benzoyl oximes with cyanoarenes to synthesize primary amines with fully substituted α-carbons. We also demonstrate that this method enables the synthesis of amines with α-trifluoromethyl functionality. Based on experimental and computational results, we propose a mechanism where the photocatalyst engages in concurrent tandem catalysis by reacting with the oxime as a triplet sensitizer in the first catalytic cycle and a reductant toward the cyanoarene in the second catalytic cycle to achieve the synthesis of hindered primary amines via heterocoupling of radicals from readily available oximes.
A novel synthesis of carboxylic acid oxime esters catalyzed by 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate
Shi, Wei,Zhang, Jiming,Zhou, Qin,Wang, Xingjian,Qi, Xiaowei,Guo, Lianyong,Ma, Wanyong,Zhou, Jianhua
, p. 7125 - 7128 (2015/04/22)
We describe a facile synthesis of carboxylic acid oxime esters in acetonitrile from the corresponding carboxylic acids and oximes catalyzed by 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate in the presence of triethylamine at room temperature under mild conditions.
Efficient and alternative approach for preparation of O-benzoyloximes using benzoyl peroxide
Kundu, Shrishnu Kumar,Rahman, Matiur,Dhara, Paritosh,Hajra, Alakananda,Majee, Adinath
experimental part, p. 1848 - 1854 (2012/04/10)
Benzoyl peroxide has been used as a mild and efficient reagent for the preparation of benzoyl ester of oxime in moderate to good yields. Copyright Taylor & Francis Group, LLC.
The Effect of Solvent on the α-Effect: Abnormal Nucleophilic Reactivity of Substituted Acetophenone Oximate Anions in Aqueous DMSO
Um, Ik-Hwan,Oh, Su-Jin,Kwon, Dong-Sook
, p. 6903 - 6906 (2007/10/02)
The nucleophilic reactivity of substituted acetophenone oximate anions decreases with increasing base strengthening ability of the substituent, resulting in a positive Hammett ρ value in H2O containing 20 mole percent DMSO.
Reaction of Trimethylsilyl Azide with C=N-O Bond
Nishiyama, Kozaburo,Miyata, Izumi
, p. 2419 - 2420 (2007/10/02)
Trimethylsilyl azide (TMSA) was reacted with an oxime ester or a Reissert salt in the presence of trimethylsilyl trifluoromethanesulfonate to give tetrazole derivative.The details of these reactions are examined.
