15368-86-2Relevant academic research and scientific papers
Phenazine-Based Donor Acceptor Systems as Organic Photocatalysts for "metal-free" C-N/C-C Cross-Coupling
Deol, Harnimarta,Singh, Gurpreet,Kumar, Manoj,Bhalla, Vandana
, p. 11080 - 11093 (2020/10/12)
With an aim to achieve a balance between ground-state and excited-state reduction potential of donor acceptor systems for efficient C-N/C-C cross-coupling, a series of donor acceptor systems DA1-DA4 have been synthesized by varying the donor strength and connecting positions. With an increase in donor strength, systematic elevation in the ground-state reduction potential and decrease in the HOMO-LUMO gap was observed. Interestingly, all the derivatives DA1-DA4 could catalyze the C-N bond formation reaction between activated aryl halides and amines at low catalytic loading under metal-free conditions without the need of any external base upon irradiation with white LED. A balance was realized in the case of derivative DA2, which exhibits high efficiency in C-N couplings. Different control experiments support the validity of the energy as well as electron transfer pathways in the visible light-mediated C-N bond formation. This study further reveals the potential of derivative DA1 in "metal-free"Sonogashira coupling involving activated aryl halides which is attributed to its high excited-state reduction potential.
Copper-Catalyzed Electrophilic Amination of Alkoxyarylsilanes
Hitoshio, Kenshiro,Saito, Hayate,Shimokawa, Jun,Yorimitsu, Hideki,Zhang, Qian
supporting information, (2020/07/04)
We report a copper-catalyzed amination reaction between simple alkoxyarylsilanes and N-benzoyloxyamines. Silver fluoride serves as a stoichiometric base as well as an indispensable activator that allows the catalytic process to proceed. Multiply alkoxylated arylsilanes, such as trialkoxyarylsilanes and dialkoxyarylsilanes were transformed into the corresponding tertiary anilines under mild reaction conditions.
Magnesium-mediated arylation of amines via C-F bond activation of fluoroarenes
Bole, Leonie J.,Davin, Laia,Kennedy, Alan R.,McLellan, Ross,Hevia, Eva
supporting information, p. 4339 - 4342 (2019/04/26)
A series of new Mg(ii) amides featuring a bulky β-diketiminate backstop ligand, has been synthesised. These complexes are demonstrated to be excellent sources of nucleophilic amides that can participate in rapid C-F activation of several fluoroarenes at room temperature or using microwave assistance, leading to the installment of synthetically important C-N bonds via nucleophilic substitution.
Copper-catalyzed electrophilic amination of heteroarenes and arenes by C-H zincation
McDonald, Stacey L.,Hendrick, Charles E.,Wang, Qiu
supporting information, p. 4667 - 4670 (2014/05/20)
Direct amination of heteroarenes and arenes has been achieved in a one-pot C-H zincation/copper-catalyzed electrophilic amination procedure. This amination method provides an efficient and rapid approach to access a diverse range of heteroaromatic and aromatic amines including those previously inaccessible using C-H amination methods. The mild reaction conditions and good functional-group compatibility demonstrate its great potential for the synthesis of important and complex amines. Direct amination of heteroarenes and arenes has been achieved in a one-pot zincation/Cu(OAc)2-catalyzed amination sequence using O-acylhydroxylamines. The method provides a rapid and efficient approach to a range of aromatic and heteroaromatic amines, including those which were previously inaccessible by using C-H amination methods. tmp=2,2,6,6- tetramethylpiperidide.
