4147-89-1Relevant articles and documents
Photo electron transfer induced desilylation of: N, N -bis(trimethylsilyl)aminodibenzoborole to aminodibenzoborole
Keck, Constanze,Maichle-Mossmer, C?cilia,Bettinger, Holger F.
, p. 7470 - 7473 (2019)
The synthesis of 9-amino-9-borafluorene is described using a photoinduced twofold desilylation of the N,N-bis(trimethylsilyl) derivative 2. The mechanistic analysis suggests an initial single electron transfer step from 2 to the halogen containing solvent. 9-Amino-9-borafluorene undergoes a photoinduced cyclooligomerization, most reasonably to the dimer.
Simple Nickel Salts for the Amination of (Hetero)aryl Bromides and Iodides with Lithium Bis(trimethylsilyl)amide
Martinez, Gabriel Espinosa,Nugent, Joseph W.,Fout, Alison R.
supporting information, p. 2941 - 2944 (2018/09/21)
Recent developments in the chemistry of C-N bond formation and the synthesis of anilines have allowed for the use of first-row transition metals to catalyze these transformations. Much of the progress in this area has been driven by comprehensive screening for privileged/tailored ligands, which can be costly and not readily available in a research laboratory setting. In this communication we report a protocol in which simple nickel salts catalyze the C-N cross-coupling reaction between (hetero)aryl bromides and iodides with lithium bis(trimethylsilyl)amide without the need for any additive ligand. This method is amenable to low nickel catalyst loadings (1%) as well as gram-scale reactions. Because of the good functional group tolerance and compatibility with heterocyclic moieties, this method is useful for academic laboratory settings where access to tailored ligands and noble-metal catalysts could be challenging.
Peculiarities of the reaction of alkali metal bis(trimethylsilyl)amides with halobenzenes
Lis,Tsyrendorzhieva,Albanov,Gostevskii,Rakhlin
, p. 2090 - 2094 (2016/10/03)
Lithium and sodium bis(trimethylsilyl)amides react with fluoro-, bromo-, and chlorobenzenes in THF or toluene to give a mixture of N,N-bis(trimethylsilyl)aniline and N,2-bis(trimethylsilyl)aniline. The latter compound is resulted from 1,3-shift of the trimethylsilyl group from nitrogen to ortho-carbon atom of the benzene ring. Effects of the solvent, halogen, and alkali metal nature as well as the reaction conditions on the ratio of isomers were examined. Reaction of iodobenzene with sodium bis(trimethylsilyl)amide in THF produces N,N-bis(trimethylsilyl)aniline and 2-iodo-N,N-bis(trimethylsilyl)aniline, while in toluene a mixture of three products, two indicated above and N,N-bis(trimethylsilyl)benzylamine, was obtained.