24517-59-7Relevant academic research and scientific papers
Cooperative Light-Activated Iodine and Photoredox Catalysis for the Amination of Csp3 ?H Bonds
Becker, Peter,Duhamel, Thomas,Stein, Christopher J.,Reiher, Markus,Mu?iz, Kilian
, p. 8004 - 8008 (2017)
An unprecedented method that makes use of the cooperative interplay between molecular iodine and photoredox catalysis has been developed for dual light-activated intramolecular benzylic C?H amination. Iodine serves as the catalyst for the formation of a n
Intermolecular 1,2-Difunctionalization of Alkenes Enabled by Fluoroamide-Directed Remote Benzyl C(sp3)-H Functionalization
Zhong, Long-Jin,Xiong, Zhi-Qiang,Ouyang, Xuan-Hui,Li, Yang,Song, Ren-Jie,Sun, Qing,Lu, Xin,Li, Jin-Heng
supporting information, p. 339 - 348 (2022/01/08)
A copper-catalyzed remote benzylic C-H functionalization strategy enabling 1,2-difunctionalization of alkenes with 2-methylbenzeneamides and nucleophiles, including alcohols, indoles, pyrroles, and the intrinsic amino groups, is reported, which is charact
Bis(trifluoromethanesulfonimide) (BSI): Acidity and application to hydrofunctionalization as a Br?nsted acid catalyst
Takagi, Ryukichi,Sakai, Yuichiro,Duong, Duyen Thi
, (2021/03/23)
A binaphthyl derivative, bearing bis(trifluoromethanesulfonimide) (BSI) moiety, was developed as a novel Br?nsted acid. Computational prediction of the pKa value of BSI indicated its classification as a strong Br?nsted acid. BSI catalyzed the h
Aniline-Type Hypervalent Iodine(III) for Intramolecular Cyclization via C?H Bond Abstraction of Hydrocarbons Containing N- and O-Nucleophiles
Nishiguchi, Yuna,Moriyama, Katsuhiko
supporting information, p. 3354 - 3358 (2021/05/17)
We developed a method for the preparation of (diacetoxyiodo)-2-(N-alkylamido)benzene as an aniline-type hypervalent iodine(III). We also achieved direct cyclizations via C?H bond abstraction, such as the Hofmann-L?ffler-Freytag reaction, a direct amination, and a direct lactonization, using the aniline-type hypervalent iodine(III) to obtain corresponding products in high yields. (Figure presented.).
Visible light bromide catalysis for oxazoline, pyrrolidine, and dihydrooxazine synthesesviaCsp3-H functionalizations
Kaur, Navdeep,Ziegelmeyer, Elizabeth C.,Farinde, Olutayo N.,Truong, Jonathon T.,Huynh, Michelle M.,Li, Wei
supporting information, p. 10387 - 10390 (2021/10/14)
A catalytic benzylic Csp3-H functionalization protocol is described here. This visible light-mediated process is centered on the utilization of a bromide catalyst and oxidant to generate a nitrogen (N)-centered radical for a site-selective hydrogen atom transfer (HAT) process. This strategy enabled the unconventional syntheses of a number of N-heterocycles dependent on the amide identity. We also discovered a nucleophilicity-dependent kinetic resolution for stereochemical differentiation of Csp3-H bonds that enabled the stereoselective synthesis ofcis- andtrans-oxazolines.
Stereospecific Synthesis of cis-2,5-Disubstituted Pyrrolidines via N, O-Acetals Formed by Hydroamination Cyclization-Hydroalkoxylation of Homopropargylic Sulfonamides in HFIP
Cao, Xiaohui,Chang, Weixing,Li, Jing,Liu, Lingyan,Shi, Xiaoyu,Wang, Weilin,Xiao, Weiguo,Zuo, Xiaodan
, p. 7045 - 7059 (2020/07/07)
We reported a novel two-step stereoselective synthesis of functionalized pyrrolidines from homopropargylic sulfonamides and nucleophiles via an isolable N,O-acetal intermediates. This reaction features mild conditions and good scope of substrates. In addition, the use of hexafluoroisopropanol, acting as a solvent, an additive, a weak nucleophile, and a good leaving group, is pivotal to the success of the method. Moreover, reactions of chiral homopropargylic sulfonamides afford only 2,5-cis-disubstituted pyrrolidines with high diastereoselectivity (up to >99:1 dr) and enantioselectivity (up to >99% ee). The overall reaction constitutes a formal 1,1-bifunctionalization of terminal alkynes, which has hitherto been reported only rarely. Additionally, this method provides efficient access to pharmaceutical intermediate and to carry out postmodification of natural products.
Redox Neutral Radical-Relay Cobalt Catalysis toward C-H Fluorination and Amination
Guo, Peng,Han, Jun-Fa,Li, Yuanyuan,Ye, Ke-Yin,Yu, Yi,Zhang, Xiang-Gui,Zhu, Jun
supporting information, (2020/05/01)
A redox neutral radical-relay cobalt-catalyzed intramolecular C-H fluorination of N-fluoroamides featuring the in situ formed cobalt fluorides as the latent radical fluorinating agents is reported. Moreover, the reactivity of such a cobalt catalysis could be diverted from C-H fluorination to amination by engineering substrates' conformational flexibility. Preliminary mechanistic studies (UV-vis spectroscopy, cyclic voltammetry studies and DFT calculations, etc.) support the reaction proceeding a redox neutral radical-relay mechanism.
TMSOTf mediated '5/6-: Endo-dig ' reductive hydroamination for the stereoselective synthesis of pyrrolidine and piperidine derivatives
Gharpure, Santosh J.,Vishwakarma, Dharmendra S.,Patel, Raj K.
, p. 6858 - 6861 (2019/06/18)
A TMSOTf mediated 5/6-endo-dig reductive hydroamination cascade on internal alkynylamines gave expedient, stereoselective access to pyrrolidine and piperidine derivatives. We also demonstrate that a protecting group on nitrogen has a profound effect on the reactivity as well as diastereoselectivity of the reductive hydroamination cascade.
Merging Photochemistry with Electrochemistry: Functional-Group Tolerant Electrochemical Amination of C(sp3)?H Bonds
Wang, Fei,Stahl, Shannon S.
, p. 6385 - 6390 (2019/03/21)
Direct amination of C(sp3)?H bonds is of broad interest in the realm of C?H functionalization because of the prevalence of nitrogen heterocycles and amines in pharmaceuticals and natural products. Reported here is a combined electrochemical/pho
Copper-Catalyzed N?F Bond Activation for Uniform Intramolecular C?H Amination Yielding Pyrrolidines and Piperidines
Bafaluy, Daniel,Mu?oz-Molina, José María,Funes-Ardoiz, Ignacio,Herold, Sebastian,de Aguirre, Adiran J.,Zhang, Hongwei,Maseras, Feliu,Belderrain, Tomás R.,Pérez, Pedro J.,Mu?iz, Kilian
supporting information, p. 8912 - 8916 (2019/05/29)
The dual function of the N?F bond as an effective oxidant and subsequent nitrogen source in intramolecular aliphatic C?H functionalization reactions is explored. Copper catalysis is demonstrated to exercise full regio- and chemoselectivity control, which
