124582-74-7Relevant academic research and scientific papers
Aminosilanes in organic synthesis. Hydrostannation of N,N-bis(trimethylsilyl)propargylamine. Facile and selective routes to (E)-allylic amines
Corriu, R.J.P.,Bolin, G.,Moreau, J.J.E.
, p. 273 - 280 (2007/10/02)
The addition of tributyl tin hydride to N,N-bis(trimethylsilyl)propargylamine yielded E-1-tributylstannyl-3-prop-1-ene 2 in 90percent yield and 96percent stereochemical purity.The functional vinyl tin reagent 2 was shown to give short and selective access to primary allylic amines.The reactions of 2 with aryl and vinyl bromides in the presence of a palladium catalyst gave substituted E-allylic amines in high yields.The reaction of 2 with butyl lithium yielded E-γ-vinyl lithium from which selective access to E-allylic amines was obtained.Key words: silylamines / propargylamines / hydrostannation / vinyl tin / vinyl lithium / (E)-allylamines
Silver iodide mediated amination reaction of allylic chlorides with lithium bis(trimethylsilyl)amide: A new synthetic method of N,N- disilylallylamines via lithium amide argentates
Murai,Yamamoto,Kondo,Kato
, p. 7440 - 7445 (2007/10/02)
The nucleophilic substitution reaction of allylic chlorides with lithium bis(trimethylsilyl)amide (1) in the presence of silver halides has been studied in detail. Silver iodide (AgI) was found to be most effective for facilitation of the amination reaction. The reaction of alkyl-substituted allylic chlorides proceeded smoothly in S(N)2 fashion to give N,N- disilylallylamines in high yields when 0.1 or 0.5 equiv of AgI was used as an additive, whereas a stoichiometric amount of AgI was indispensable in the reaction of allylic chlorides having a phenyl group. The reaction of geranyl or neryl chloride proceeded with retention of configuration of the C=C bond to give only one isomer 4 or 5, respectively. The oxygen-containing functional groups and chlorine remained intact during the reaction. The reaction of α-silylmetallyl chloride 17 proceeded in an S(N)2' manner to afford (Z)-allylamine 18. So as to disclose the active species in the AgI- mediated reaction, the variable low-temperature 13C NMR experiments using the mixture of AgI and 1 in THF have been performed. It has been suggested that lithium amide argentates such as (Me3Si)2NAg(I)Li (20) and [(Me3Si)2N]2Ag(I)Li2 (21) are formed in the reaction mixture, and the nucleophilicity and basicity of 1 are controlled by forming these species.
A simple synthesis of primary E-allylic amines from 1-tributylstannyl-3-bis(trimethylsilyl)amino prop-1-ene
Corriu,Bolin,Moreau
, p. 4121 - 4124 (2007/10/02)
A facile and selective preparation of primary E-allylic amines is described from the readily available γ-amino vinylic tin reagent 2, either by using the direct palladium catalysed coupling of the vinyl tin moitie or via conversion to a γ-amino vinyl lithium reagent.
Cobalt Carbonyl Catalyzed Hydrosilylation of Nitriles: A New Preparation of N,N-Disilylamines
Murai, Toshiaki,Sakane, Takehiko,Kato, Shinzi
, p. 449 - 453 (2007/10/02)
Cobalt carbonyl catalyzed hydrosilylation of a wide variety of nitriles with HSiMe3 has been examined.The reaction generally proceeded at 60 deg C to give N,N-disilylamines in good yields.Electron-donating groups on aromatic nitriles facilitated the react
Amination Reaction of Allylic Chlorides with Silver Iodide/Lithium N,N-Disilylamide Mixed Reagents
Murai, Toshiaki,Yamamoto, Mikio,Kato, Shinzi
, p. 789 - 790 (2007/10/02)
The nucleophilic substitution of allylic chlorides with silver iodide/lithium N,N-disilylamide mixed reagents gives protected primary amines in good to excellent yields.
