24907-33-3Relevant academic research and scientific papers
α-Tertiary Propargylamine Synthesis via KA2-Type Coupling Reactions under Solvent-Free CuI-Zeolite Catalysis
Bénéteau, Valérie,Chassaing, Stefan,Pale, Patrick,Plac?is, Clotilde,Schlimpen, Fabian,Starck, Eliot
, p. 16593 - 16613 (2021/12/06)
The potential of copper(I)-zeolite catalysis was evaluated in the three-component KA2-coupling mediated synthesis of α-tertiary propargylamines. Our archetypal copper(I)-doped zeolite CuI-USY proved to be efficient under ligand- A nd solvent-free conditions at 80 °C. Usable up to four times, this catalytic material enables the coupling of diverse ketones, alkynes, and amines with a broad functional group tolerance. A decarboxylative and a desilylative version, respectively, involving an alkynoic acid and trimethylsilylacetylene as alkyne surrogates, was also set up to bypass selectivity issues and/or to access α-tertiary propargylamines that are unattainable under standard KA2 conditions. Interestingly, the KA2-type coupling reactions were successfully linked to other CuI-catalyzed reactions, thus resulting in sequential one-pot processes under full CuI-USY catalysis.
Formation of α-Monosubstituted propargylamines from terminal alkynes and secondary amines using a (PNO)Rh/Cu Tandem catalyst system
Takano, Shotaro,Kochi, Takuya,Kakiuchi, Fumitoshi
supporting information, p. 1620 - 1623 (2017/11/04)
A novel (PNO)Rh/CuBr (PNO: phosphine-quinolinolate) tandem catalyst system was developed for facile synthesis of α-monosubstituted propargylamines from aliphatic terminal al-kynes and secondary amines. Various terminal alkynes and amines were applicable t
Synthesis of propargylamines by a copper-catalyzed tandem anti-Markovnikov hydroamination and alkyne addition
Zhou, Lei,Bohle, D. Scott,Jiang, Huan-Feng,Li, Chao-Jun
scheme or table, p. 937 - 940 (2009/09/06)
A highly efficient tandem anti-Markovnikov hydroamination and alkyne addition reaction catalyzed by a Cu(I) or Cu(II) catalyst was developed. Various propargylamines were obtained in moderate to good yields. This tandem process provides a novel and simple approach to propargylamine derivatives from alkynes and amines.
Zn(OAc)2·2H2O: a versatile catalyst for the one-pot synthesis of propargylamines
Ramu, Enugala,Varala, Ravi,Sreelatha, Nuvula,Adapa, Srinivas R.
, p. 7184 - 7190 (2008/03/11)
An inexpensive and readily available catalyst, Zn(OAc)2·2H2O is successfully evaluated for effective one-pot synthesis of propargylamines with moderate to excellent yields for most of the substrates screened, without the need of base, co-catalyst or additive in the presence of air.
Amination of aryl- and vinylacetylenic compounds catalyzed by rhodium(I) complexes
Costa,Chiusoli,Gaetti,Gabriele,Salerno
, p. 936 - 940 (2007/10/03)
New rhodium-catalyzed amination reactions of arylacetylenes and cyclohexen-1-ylacetylene in the presence of strong bases with the use of carbon dioxide as an auxiliary are described. Secondary amines attack the terminal carbon atom of the triple bond followed by protonation of the adjacent carbon atom. Alternatively, the reaction can proceed further with the addition of the second alkyne molecule. The conditions for the selective synthesis of enamines (up to 87% yield) or α-substituted propynylamines (up to 86% yield) are reported.
