17299-11-5Relevant academic research and scientific papers
Ni-Catalyzed Reductive Coupling of Electron-Rich Aryl Iodides with Tertiary Alkyl Halides
Wang, Xuan,Ma, Guobin,Peng, Yu,Pitsch, Chloe E.,Moll, Brenda J.,Ly, Thu D.,Wang, Xiaotai,Gong, Hegui
supporting information, p. 14490 - 14497 (2018/11/02)
This work illustrates the reductive coupling of electron-rich aryl halides with tertiary alkyl halides under Ni-catalyzed cross-electrophile coupling conditions, which offers an efficient protocol for the construction of all carbon quaternary stereogenic centers. The mild and easy-to-operate reaction tolerates a wide range of functional groups. The utility of this method is manifested by the preparation of cyclotryptamine derivatives, wherein successful incorporation of 7-indolyl moieties is of particular interest as numerous naturally occurring products are composed of these key scaffolds. DFT calculations have been carried out to investigate the proposed radical chain and double oxidative addition pathways, which provide useful mechanistic insights into the part of the reaction that takes place in solution.
Regio- and Stereoselective Synthesis of β-Halohydrins from 1,2-Epoxides with Ammonium Halides in the Presence of Metal Salts
Chini, Marco,Crotti, Paolo,Gardelli, Cristina,Macchia, Franco
, p. 3805 - 3812 (2007/10/02)
A simple efficient, stereoselective, and regioselective method for the synthesis of β-chlorohydrins, β-bromohydrins, and β-iodohydrins by the direct opening of 1,2-epoxides with the corresponding ammonium halide in acetonitrile, in the presence of metal salts, is described.This new method appears to be of general use and competitive with the other methods previously reported.
