79796-59-1Relevant academic research and scientific papers
Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions
Barraza, Scott J.,Denmark, Scott E.
, p. 2891 - 2895 (2017/10/06)
Alkylation of 2-bromoaniline with benzyl bromide under ostensibly basic N-alkylation conditions resulted in migration of bromine from the 2- to the 4-aryl position. Herein we report our studies to elucidate the mechanism of this rearrangement with the objective of suppressing this unexpected outcome. We find that careful choice of reagents is critical, and that this behavior may be extrapolated to alkylation reactions of electron-rich bromo- and iodoanilines in general.
Transition metal-free N-arylation of secondary amides through iodonium salts as aryne precursors
Wang, Ming,Huang, Zhijian
supporting information, p. 10185 - 10188 (2016/11/11)
By using a diaryliodonium salt as a benzyne precursor, a transition metal-free approach for N-arylation of secondary amides is developed. This novel benzyne precursor, which can be prepared easily by a one step process from an aryl iodide, shows different reactivities with previous benzyne precursors in the N-arylation reaction. Mechanistic studies confirm the involvement of benzyne species (generated in situ from the diaryliodonium salts) as key intermediates.
