5331-48-6Relevant articles and documents
Pillar[5]arenes with an introverted amino group: A hydrogen bonding tuning effect
Chen, Lei,Li, Zhiming,Chen, Zhenxia,Hou, Jun-Li
, p. 248 - 251 (2013)
Pillar[5]arenes with introverted amino groups were produced through aminolysis. X-ray analysis demonstrated that the intramolecular hydrogen bonding induced the amino group toward the inner space of the cavity. The kinetic studies and molecular modelings revealed that the hydrogen bonding also contributed to the acceleration of the aminolysis through stabilizing the intermediate.
Decarboxylative Ritter-Type Amination by Cooperative Iodine (I/III)─Boron Lewis Acid Catalysis
Narobe, Rok,Murugesan, Kathiravan,Schmid, Simon,K?nig, Burkhard
, p. 809 - 817 (2022/01/15)
Recent years have witnessed important progress in synthetic strategies exploiting the reactivity of carbocations via photochemical or electrochemical methods. Yet, most of the developed methods are limited in their scope to certain stabilized positions in molecules. Herein, we report a metal-free system based on the iodine (I/III) catalytic manifold, which gives access to carbenium ion intermediates also on electronically disfavored benzylic positions. The unusually high reactivity of the system stems from a complexation of iodine (III) intermediates with BF3. The synthetic utility of our decarboxylative Ritter-type amination protocol has been demonstrated by the functionalization of benzylic as well as aliphatic carboxylic acids, including late-stage modification of different pharmaceutical molecules. Notably, the amination of ketoprofen was performed on a gram scale. Detailed mechanistic investigations by kinetic analysis and control experiments suggest two mechanistic pathways.
Monoacylation of Symmetrical Diamines in Charge Microdroplets
Ansu-Gyeabourh, Emelia,Amoah, Enoch,Ganesa, Chandrashekar,Badu-Tawiah, Abraham K.
, p. 531 - 536 (2021/01/13)
Monoacylation of symmetrical diamine is achieved when the primary α,ω-diamines (carbon numbers n = 3, 5 and 12) are diluted in ethyl acetate, and the resultant mixture is electrosprayed across a 10 mm distance in ambient air toward a mass spectrometer. The N-acylated product is formed in charged microdroplets without acidifying and activating agents and in the absence of heat. This result provided an insight into the orientation of the amines in the droplets, suggesting that the ester is activated to react with the amine at the droplet surface due to the high abundance of protons at the air-droplet interface.
Synthesis of diverse libraries of carboxamides via chemoselective N-acylation of amines by carboxylic acids employing Br?nsted acidic IL [BMIM(SO3H)][OTf]
Savanur, Hemantkumar M.,Malunavar, Shruti S.,Prabhala, Pavankumar,Sutar, Suraj M.,Kalkhambkar, Rajesh G.,Laali, Kenneth K.
supporting information, (2019/09/30)
Chemoselective N-acylation of amines with carboxylic acids as acyl electrophiles and Br?nsted acidic IL [BMIM(SO3H)][OTf] as promoter is reported under both thermal and microwave irradiation to produce libraries of carboxamides in good to excellent yields after a simple workup. The protocol is compatible with structurally diverse 1° and 2° amines and works in the presence of sensitive functional groups such as thiols and phenols. The potential for recycling and reuse of the IL is also demonstrated.
