1220099-13-7Relevant articles and documents
Triarylborane catalysed: N-alkylation of amines with aryl esters
Ariafard, Alireza,Babaahmadi, Rasool,Carlone, Armando,Dasgupta, Ayan,Melen, Rebecca L.,Nori, Valeria
, p. 7523 - 7530 (2020/11/27)
The ability of halogenated triarylboranes to accept a lone pair of electrons from donor substrates renders them excellent Lewis acids which can be exploited as a powerful tool in organic synthesis. Tris(pentafluorophenyl)borane has successfully demonstrated its ability to act as a metal-free catalyst for an ever-increasing range of organic transformations. Herein we report the N-alkylation reactions of a wide variety of amine substrates including diarylamines, N-methylphenyl amines, and carbazoles with aryl esters using catalytic amounts of B(C6F5)3. This mild reaction protocol gives access to N-alkylated products (35 examples) in good to excellent yields (up to 95%). The construction of a C-N bond at the propargylic position has also been demonstrated to yield synthetically useful propargyl amines. On the other hand, unsubstituted 1H-indoles and 1H-pyrroles at the C3/C2 positions afforded exclusively C-C coupled products. Extensive DFT studies have been employed to understand the mechanism for this transformation.
Commercially available simple ionic liquids-promoted dehydrative carbon-carbon bond-forming reaction of diarylmethanols and triarylmethanols with pyrroles, thiophene, furan and indoles
Funabiki, Kazumasa,Komeda, Takuya,Nishikawa, Kouhei,Yamada, Kentaro,Kubota, Yasuhiro,Matsui, Masaki
, p. 9245 - 9252 (2015/02/19)
Two commercially available simple ionic liquids, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate and 1-ethyl-2,3-dimethylimidazolium trifluoromethansulfonate, effectively promote the solvent-free dehydrative carbon-carbon (C-C) bond-forming reaction
