864512-14-1Relevant articles and documents
Synthesis of Stannylated Aryl Imines and Amines via Aryne Insertion Reactions into Sn?N Bonds
Kran, Eva,Mück-Lichtenfeld, Christian,Daniliuc, Constantin G.,Studer, Armido
supporting information, p. 9281 - 9285 (2021/05/31)
The reaction of in situ generated arynes with stannylated imines to provide ortho-stannyl-aniline derivatives is reported. The readily prepared trimethylstannyl benzophenone imine is introduced as an efficient reagent to realize the aryne σ-insertion reaction. The imine functionality is an established N-protecting group and insertions proceed with good yields and good to excellent regioselectivities. The product anilines are valuable starting materials for follow-up chemistry thanks to the rich chemistry offered by the trimethylstannyl moiety.
Double heteroatom functionalization of arenes using benzyne three-component coupling
Garca-Lpez, Jos-Antonio,etin, Meliha,Greaney, Michael F.
supporting information, p. 2156 - 2159 (2015/02/19)
Arynes participate in three-component coupling reactions with N, S, P, and Se functionalities to yield 1,2-heteroatom-difunctionalized arenes. Using 2-iodophenyl arylsulfonates as benzyne precursors, we could effectively add magnesiated S-, Se-, and N-nucleophilic components to the strained triple bond. In the same pot, addition of electrophilic N, S, or P reagents and a copper(I) catalyst trapped the intermediate aryl Grignard to produce a variety of 1,2- difunctionalized arenes.