4662-96-8Relevant articles and documents
Reactions of benzyltriphenylphosphonium salts under photoredox catalysis
Boldt, Andrew M.,Dickinson, Sidney I.,Ramirez, Jonathan R.,Benz-Weeden, Anna M.,Wilson, David S.,Stevenson, Susan M.
, p. 7810 - 7815 (2021/09/28)
The development of benzyltriphenylphosphonium salts as alkyl radical precursors using photoredox catalysis is described. Depending on substituents, the benzylic radicals may couple to form C-C bonds or abstract a hydrogen atom to form C-H bonds. A natural product, brittonin A, was also synthesized using this method.
Ni-Catalyzed Iterative Alkyl Transfer from Nitrogen Enabled by the in Situ Methylation of Tertiary Amines
Nwachukwu, Chideraa Iheanyi,McFadden, Timothy Patrick,Roberts, Andrew George
, p. 9979 - 9992 (2020/09/03)
Current methods to achieve transition-metal-catalyzed alkyl carbon-nitrogen (C-N) bond cleavage require the preformation of ammonium, pyridinium, or sulfonamide derivatives from the corresponding alkyl amines. These activated substrates permit C-N bond cleavage, and their resultant intermediates can be intercepted to affect carbon-carbon bond-forming transforms. Here, we report the combination of in situ amine methylation and Ni-catalyzed benzalkyl C-N bond cleavage under reductive conditions. This method permits iterative alkyl group transfer from tertiary amines and demonstrates a deaminative strategy for the construction of Csp3-Csp3 bonds. We demonstrate PO(OMe)3 (trimethylphosphate) to be a Ni-compatible methylation reagent for the in situ conversion of trialkyl amines into tetraalkylammonium salts. Single, double, and triple benzalkyl group transfers can all be achieved from the appropriately substituted tertiary amines. Transformations developed herein proceed via recurring events: The in situ methylation of tertiary amines by PO(OMe)3, Ni-catalyzed C-N bond cleavage, and concurrent Csp3-Csp3 bond formation.
Visible-Light-Driven Self-Coupling of Methylarenes Catalyzed by Ni2P?Cd0.5Zn0.5S Nanoparticles
Yang, Dan-Dan,Hu, Jia-Jun,Zhang, Hong,Lv, Xiao-Jun,Chen, Yong,Fu, Wen-Fu
, p. 1384 - 1392 (2020/01/08)
The Ni2P?Cd0.5Zn0.5S nanoparticles photocatalyzed self-coupling of p-xylene was reported here, and the corresponding coupling product 1,2-di-p-tolylethane was obtained. The reaction could be extended to toluene derivatives with electron-donating and electron-withdrawing substituents. Ni2P?Cd0.5Zn0.5S nanoparticles had already been characterized by XRD, ICP-AES, SEM, TEM, UV/Vis, FL, XPS. The Mott–Schottky curves of Ni2P?Cd0.5Zn0.5S were made through electrochemical methods. An active carbon free-radical was captured through ESR measurement under irradiation. The research demonstrated this photocatalytic system feasible for the self-coupling reaction of toluene derivatives.
