14618-33-8Relevant academic research and scientific papers
N-alkylation of phthalimide, carboxamide, and sulfonamides by oxdation-reduction condensation using di-tert-butyl-1,4-benzoquinone and alkyl diphenylphosphinite
Mukaiyama, Teruaki,Aoki, Hidenori
, p. 142 - 143 (2005)
Various N-alkylamides were obtained in high yields under mild conditions by treating alkyl diphenylphosphinite with phthalimide, carboxamide or sulfonamides in the presence of 2,6-di-tert-butyl-1,4-benzoquinone (DBBQ) by oxdation-reduction condensation. C
A convenient trifluoroacetylation reagent: N- (trifluoroacetyl)succinimide
Katritzky, Alan R.,Yang, Baozhen,Guofang, Qiu,Zhang, Zhongxing
, p. 55 - 57 (1999)
N-(Trifluoroacetyl)succinimide, easily prepared from trifluoroacetic anhydride and succinimide forms a novel, convenient trifluoroacetylating reagent. It trifluoroacetylates alcohols, phenols and mines, to generate trifluoroacetate esters, and trifluoroacetamides in excellent yields with very efficient work up procedures.
Electrochemical approach to trifluoroacetamide synthesis from 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) catalyzed by B12complex
Moniruzzaman, Mohammad,Yano, Yoshio,Ono, Toshikazu,Hisaeda, Yoshio,Shimakoshi, Hisashi
, (2021/03/09)
One-pot synthetic approach to produce trifluoroacetamide has been developed using an electrochemical method with the B12 complex as a catalyst under mild conditions, in open air at room temperature. Thirty examples of trifluoroacetamide were synthesized from 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) in moderate to good yields. This user-friendly strategy is compatible with a broad range of trifluoroacetamide syntheses.
Oxidative Amide Coupling from Functionally Diverse Alcohols and Amines Using Aerobic Copper/Nitroxyl Catalysis
Piszel, Paige E.,Vasilopoulos, Aristidis,Stahl, Shannon S.
supporting information, p. 12211 - 12215 (2019/07/31)
The aerobic Cu/ABNO catalyzed oxidative coupling of alcohols and amines is highlighted in the synthesis of amide bonds in diverse drug-like molecules (ABNO=9-azabicyclo[3.3.1]nonane N-oxyl). The robust method leverages the privileged reactivity of alcohol
Catalytic reduction of amides to amines by electrophilic phosphonium cations via FLP hydrosilylation
Augurusa, Alessandra,Mehta, Meera,Perez, Manuel,Zhu, Jiangtao,Stephan, Douglas W.
supporting information, p. 12195 - 12198 (2016/10/21)
A catalytic methodology for the conversion of amides to amines is reported. Of the 25 examples described, 14 examples involve the reduction of N-trifluoroacetamides to the corresponding trifluoroethylamines. These reductions are achieved by catalytic hydrosilylation of the amide mediated by an electrophilic phosphonium cation (EPC) catalyst.
An efficient method for the preparation of N-alkylamides from alkyl diphenylphosphinites and amides by using methyl acrylate
Aoki, Hidenori,Mukaiyama, Teruaki
, p. 456 - 457 (2007/10/03)
N,N-Dibenzyltrifluoroacetamide was formed in good yield by treating benzyl diphenylphosphinite with N-benzyltrifluoroacetamide in the presence of easily available methyl acrylate under mild conditions. Yields obtained for the corresponding inverted sulfon
N,N,N',N'-Tetramethylazodicarboxamide (TMAD), A New Versatile Reagent for Mitsunobu Reaction. Its Application to Synthesis of Secondary Amines
Tsunoda, Tetsuto,Otsuka, Junko,Yamamiya, Yoshiko,Ito, Sho
, p. 539 - 542 (2007/10/02)
N,N,N',N'-Tetramethylazodicarboxamide, (TMAD), was found to be more versatile in the Mitsunobu reaction than traditional diethyl azodicarboxylate or recently developed 1,1'-(azodicarbonyl)dipiperidine, when used in combination with tributylphosphine in benzene.The usefulness of the reagent was demonstrated by the highly efficient two-step synthesis of benzylcrotylamine from N-benzyltrifluoroacetamide.
Novel reactivity of stabilized methylenetributylphosphorane: A new mitsunobu reagent
Tsunoda, Tetsuto,Ozaki, Fumie,Ito, Sho
, p. 5081 - 5082 (2007/10/02)
Cyanomethylenetributylphosphorane was shown to mediate the direct condensation of alcohols with O- and N-nucleophiles. A secondary alcohol, 2- octanol, reacted satisfactorily with Walden inversion of its carbinyl carbon.
1,1′-(azodicarbonyl)dipiperidine-tributylphosphine, a new reagent system for mitsunobu reaction
Tsunoda, Tetsuto,Yamamiya, Yoshiko,Ito, Sho
, p. 1639 - 1642 (2007/10/02)
The 1,1′-(azodicarbonyl)dipiperidine (ADDP)-tributylphosphine (TBP) system was developed as a new institute of the Mitsunobu reagent. The new system activates nitrogen or carbon nucleophiles, known to be innert or poorly reactive with the Mitsunobu reagent, to react with alcohols satisfactorily forming C-N or C-C bonds. The inversion of stereogenic carbinyl carbons was confirmed in the acylaltion reaction of two sec-alcohols.
A CONVENIENT SYNTHESIS OF N-ALKYL AND N,N-DIALKYLTRIFLUOROACETAMIDES IN A SOLID-LIQUID TWO-PHASE SYSTEM IN THE PRESENCE OF PHASE-TRANSFER CATALYSTS
Landini, Dario,Penso, Michele
, p. 791 - 800 (2007/10/02)
Trifluoroacetamide is easily monoalkylated in a K2CO3-organic solvent solid-liquid two-phase system affording in good to excellent yields N-alkyltrifluoroacetamides.Under the same conditions, the latter, in turn, ract with alkylating agents giving N,N-dialkyltrifluoroacetamides in high yields.
