772-70-3Relevant articles and documents
Ruthenium-catalyzed intramolecular arene C(sp2)-H amidation for synthesis of 3,4-dihydroquinolin-2(1 H)-ones
Au, Chi-Ming,Ling, Cho-Hon,Sun, Wenlong,Yu, Wing-Yiu
supporting information, p. 3310 - 3314 (2021/05/29)
We report the [Ru(p-cymene)(l-proline)Cl] ([Ru1])-catalyzed cyclization of 1,4,2-dioxazol-5-ones to form dihydroquinoline-2-ones in excellent yields with excellent regioselectivity via a formal intramolecular arene C(sp2)-H amidation. The reactions of the 2- and 4-substituted aryl dioxazolones proceeds initially through spirolactamization via electrophilic amidation at the arene site, which is para or ortho to the substituent. A Hammett correlation study showed that the spirolactamization is likely to occur by electrophilic nitrenoid attack at the arene, which is characterized by a negative ρ value of -0.73.
A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines
Ni, Shengyang,Padial, Natalia M.,Kingston, Cian,Vantourout, Julien C.,Schmitt, Daniel C.,Edwards, Jacob T.,Kruszyk, Monika M.,Merchant, Rohan R.,Mykhailiuk, Pavel K.,Sanchez, Brittany B.,Yang, Shouliang,Perry, Matthew A.,Gallego, Gary M.,Mousseau, James J.,Collins, Michael R.,Cherney, Robert J.,Lebed, Pavlo S.,Chen, Jason S.,Qin, Tian,Baran, Phil S.
supporting information, p. 6726 - 6739 (2019/05/06)
Historically accessed through two-electron, anionic chemistry, ketones, alcohols, and amines are of foundational importance to the practice of organic synthesis. After placing this work in proper historical context, this Article reports the development, f
Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis
Ackerman, Laura K. G.,Martinez Alvarado, Jesus I.,Doyle, Abigail G.
, p. 14059 - 14063 (2018/10/24)
A method for direct cross coupling between unactivated C(sp3)-H bonds and chloroformates has been accomplished via nickel and photoredox catalysis. A diverse range of feedstock chemicals, such as (a)cyclic alkanes and toluenes, along with late-stage intermediates, undergo intermolecular C-C bond formation to afford esters under mild conditions using only 3 equiv of the C-H partner. Site selectivity is predictable according to bond strength and polarity trends that are consistent with the intermediacy of a chlorine radical as the hydrogen atom-abstracting species.