4383-27-1Relevant articles and documents
Reductive Alkylation of Azides and Nitroarenes with Alcohols: A Selective Route to Mono- And Dialkylated Amines
Borthakur, Ishani,Maji, Milan,Joshi, Abhisek,Kundu, Sabuj
, p. 628 - 643 (2021/12/27)
Herein, we demonstrated an efficient protocol for reductive alkylation of azides/nitro compounds via a borrowing hydrogen (BH) method. By following this protocol, selective mono- and dialkylated amines were obtained under mild and solvent-free conditions. A series of control experiments and deuterium-labeling experiments were performed to understand this catalytic process. Mechanistic studies suggested that the Ir(III)-H was the active intermediate in this reaction. KIE study revealed that the breaking of the C-H bond of alcohol might be the rate-limiting step. Notably, this solvent-free strategy disclosed a high TON of around 5600. Based on kinetic studies and control experiments, a metal-ligand cooperative mechanism was proposed.
Consecutive β,β′-Selective C(sp3)?H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C6F5)3
Fang, Huaquan,Xie, Kaixue,Kemper, Sebastian,Oestreich, Martin
supporting information, p. 8542 - 8546 (2021/03/08)
Tris(pentafluorophenyl)borane has been found to catalyze the two-fold C(sp3)?H silylation of various trialkylamine derivatives with dihydrosilanes, furnishing the corresponding 4-silapiperidines in decent yields. The multi-step reaction cascade involves amine-to-enamine dehydrogenation at two alkyl residues and two electrophilic silylation reactions of those enamines, one inter- and one intramolecular.
Direct benzylation of amines with benzylic alcohols catalyzed by palladium/phosphine-borane catalyst system
Onodera, Gen,Kumagae, Hidenobu,Nakamura, Daiki,Hayasaki, Takuto,Fukuda, Tsutomu,Kimura, Masanari
supporting information, (2020/11/04)
Direct catalytic benzylation of amines with benzylic alcohols to give benzylamines has been newly developed by using palladium/phosphine-borane catalyst system. In this catalytic reaction, the linking between both phosphine and borane moieties in the ligand is very important. Hydroxy group of benzylic alcohols is activated by Lewis acidic borane to form a benzylpalladium intermediate which is attacked by amines to give benzylamine products.