A new highly efficient and reusable Cu（I）-MOF has been developed for the synthesis of propargylamine compounds via the three-component reaction of secondary amines, alkynes, and aromatic aldehydes under solvent-free...A new highly efficient and reusable Cu（I）-MOF has been developed for the synthesis of propargylamine compounds via the three-component reaction of secondary amines, alkynes, and aromatic aldehydes under solvent-free conditions. The desired propargylamines were obtained in good to excellent yields with a low catalyst loading. The catalyst may be recovered and reused for up to 5 cycles without major loss of activity. This protocol has the advantages of excellent yields, low catalyst loading, and catalyst recyclability.展开更多
A facile,one-pot synthesis of N-aryl propargylamine from aromatic boronic acid,aqueous ammonia,and propargyl bromide has been achieved under microwave-assisted conditions.The reactions can be smoothly completed within...A facile,one-pot synthesis of N-aryl propargylamine from aromatic boronic acid,aqueous ammonia,and propargyl bromide has been achieved under microwave-assisted conditions.The reactions can be smoothly completed within a total 10 min through a two-step procedure,including copper-catalyzed coupling of aromatic boronic acids with aqueous ammonia and following propargylation by propargyl bromide.展开更多
A one pot three‐component coupling reaction of phenylacetylene, aldehyde, and amine derivatives in the presence of Cu(II) Salen complex as an efficient heterogeneous catalyst under solvent‐free conditions is reporte...A one pot three‐component coupling reaction of phenylacetylene, aldehyde, and amine derivatives in the presence of Cu(II) Salen complex as an efficient heterogeneous catalyst under solvent‐free conditions is reported. The catalyst displayed high activity and afforded the corresponding propargylamines in good to excellent yields. This method provides a wide range of substrate applicability. The catalyst was reused several times without significant loss of its catalytic activity.展开更多
The bicyclic product containing a chromene skeleton and a propargylamine skeleton（C（22）H（22）N2O2） was synthesized from the double sites of terminal alkyne, piperazine derivative and formaldehyde via one-pot proc...The bicyclic product containing a chromene skeleton and a propargylamine skeleton（C（22）H（22）N2O2） was synthesized from the double sites of terminal alkyne, piperazine derivative and formaldehyde via one-pot procedure. Its structure was characterized by ^1H NMR, ^13C NMR, IR and H RMS, and further confirmed by single-crystal X-ray diffraction. It crystallizes in the monoclinic system, space group P21/n with a = 12.6571（14）, b = 11.3249（12）, c = 12.6571（14） A, β = 105.22°,V = 1750.6（3） A^3, Z = 4, R = 0.0568 and w R = 0.1444. The fluorescence of the product was discussed.展开更多
Stereoselective approach for preparation ofα-difluoromethylα-propargylamines has been developed.1,2-Addition of lithium acetylides to diverse chiral difluoromethylated（S）-N-tert-butanesulfinyl ketimines by using T...Stereoselective approach for preparation ofα-difluoromethylα-propargylamines has been developed.1,2-Addition of lithium acetylides to diverse chiral difluoromethylated（S）-N-tert-butanesulfinyl ketimines by using Ti（O^iPr）_4 as catalyst and THF as solvent afforded N-tert-butanesulfinamides in good to excellent yields（51-93%） and good diastereoselectivities（dr.85：15 to 93：7）.The N-tert -butanesulfinyl group can be readily cleaved under mild acidic condition（4 mol/L HCl in dioxane） to provide the correspondingα-difiuoromethylα-propargylamine in excellent yields（90-95%）.展开更多
The construction of an unprecedented intertwined spiral solvent channel is driven by weak C–Cl…O and C–H…N interactions based on extraordinary parallel spirals which were structured from supramolecular synthon mac...The construction of an unprecedented intertwined spiral solvent channel is driven by weak C–Cl…O and C–H…N interactions based on extraordinary parallel spirals which were structured from supramolecular synthon macrocycle 1（C44H44N4O4） with a propargylamine backbone. The product is characterized by ^1H NMR, ^13C NMR, IR and HRMS, and further confirmed by single-crystal X-ray diffraction. It crystallizes in the monoclinic system, space group C2/c, with a = 28.922（3）, b = 8.5069（9）, c = 21.687（2）A^°, β = 130.6320（10）°, V = 4049.4（7） A^°3 and Z = 8. A total of 11874 reflections were collected, of which 4942 were independent（Rint = 0.0590） and 2937 were observed with I 〉 2σ（I）. The final full-matrix least-squares refinement gave R（I 〉 2s（I）） = 0.069 and w R = 0.167, S = 1.05,（Δρ）max = 0.20 and（Δρ）min =-0.22 e·A^1-3. The fluorescence of the product is discussed.展开更多
Highly active and stable magnetic copper catalysts were successfully achieved by magnetic induced Stober method and subsequent hydrothermal reaction with copper ions in alkaline condition.The high content of Cu2+as we...Highly active and stable magnetic copper catalysts were successfully achieved by magnetic induced Stober method and subsequent hydrothermal reaction with copper ions in alkaline condition.The high content of Cu2+as well as the unique structures of hierarchical copper silicate in the as-prepared catalysts endowed their outstanding catalytic performance.Efficient decarboxylative A3-coupling of a-keto acid,amine and alkyne was realized with the low Fe3 O4@CuSiO3 loading.A range of propargylamines were produced in good to excellent yields under solvent-free condition.Moreover,the catalyst can be easily separated from the final organic product with an external magnet.Also,this kind of catalyst could be recycled up to six times while maintaining its activity.展开更多
Several simple, fast and practical protocols have been developed to synthesize internal or terminal propargylamines and chalcones via A^(3)-coupling reaction of aldehydes, amines, and alkynes catalyzed by an easily av...Several simple, fast and practical protocols have been developed to synthesize internal or terminal propargylamines and chalcones via A^(3)-coupling reaction of aldehydes, amines, and alkynes catalyzed by an easily available catalyst Ag_(2)CO_(3)under solvent-free condition. The reaction proceeded smoothly to deliver various products in good-to-excellent yields with good functional group tolerance. Gram-scale preparation, bioactive molecule synthesis and asymmetric substrates have been demonstrated. Furthermore,plausible mechanisms for the synthesis of different products have been proposed.展开更多
基金financial support of this research from the Welch Foundation(No.AX-1730 for B.C.and.No. AX-1593 for J.C.-G.Z.)
文摘A new highly efficient and reusable Cu（I）-MOF has been developed for the synthesis of propargylamine compounds via the three-component reaction of secondary amines, alkynes, and aromatic aldehydes under solvent-free conditions. The desired propargylamines were obtained in good to excellent yields with a low catalyst loading. The catalyst may be recovered and reused for up to 5 cycles without major loss of activity. This protocol has the advantages of excellent yields, low catalyst loading, and catalyst recyclability.
基金the National Natural Science Foundation of China (No. 21262020)the Science and Technology Planning Project of Yunnan Province (No. KKSY201207140)+1 种基金the Natural Science Foundation of Yunnan Education Department (No. 09Y0081)the Analysis and Measurement Foundation of Kunming University of Science and Technology (No. 20130560) for their financial supports
文摘A facile,one-pot synthesis of N-aryl propargylamine from aromatic boronic acid,aqueous ammonia,and propargyl bromide has been achieved under microwave-assisted conditions.The reactions can be smoothly completed within a total 10 min through a two-step procedure,including copper-catalyzed coupling of aromatic boronic acids with aqueous ammonia and following propargylation by propargyl bromide.
文摘A one pot three‐component coupling reaction of phenylacetylene, aldehyde, and amine derivatives in the presence of Cu(II) Salen complex as an efficient heterogeneous catalyst under solvent‐free conditions is reported. The catalyst displayed high activity and afforded the corresponding propargylamines in good to excellent yields. This method provides a wide range of substrate applicability. The catalyst was reused several times without significant loss of its catalytic activity.
基金supported by the Natural Science Foundation of Anhui Province Education Department(No.KJ2014A141)the National Natural Science Foundation of China(No.21171008)
文摘The bicyclic product containing a chromene skeleton and a propargylamine skeleton（C（22）H（22）N2O2） was synthesized from the double sites of terminal alkyne, piperazine derivative and formaldehyde via one-pot procedure. Its structure was characterized by ^1H NMR, ^13C NMR, IR and H RMS, and further confirmed by single-crystal X-ray diffraction. It crystallizes in the monoclinic system, space group P21/n with a = 12.6571（14）, b = 11.3249（12）, c = 12.6571（14） A, β = 105.22°,V = 1750.6（3） A^3, Z = 4, R = 0.0568 and w R = 0.1444. The fluorescence of the product was discussed.
基金The Shanghai Pujiang Program(No09PJ1400800)the Fundamental Research Funds for the Central Universities and the Scientific Research Foundation for the Returned Overseas Chinese Scholars,State Education Ministry
文摘Stereoselective approach for preparation ofα-difluoromethylα-propargylamines has been developed.1,2-Addition of lithium acetylides to diverse chiral difluoromethylated（S）-N-tert-butanesulfinyl ketimines by using Ti（O^iPr）_4 as catalyst and THF as solvent afforded N-tert-butanesulfinamides in good to excellent yields（51-93%） and good diastereoselectivities（dr.85：15 to 93：7）.The N-tert -butanesulfinyl group can be readily cleaved under mild acidic condition（4 mol/L HCl in dioxane） to provide the correspondingα-difiuoromethylα-propargylamine in excellent yields（90-95%）.
基金supported by the Natural Science Foundation of Anhui Province Education Department(No.KJ2014A141,No.KJ2015A243,No.KJ2016A862)
文摘The construction of an unprecedented intertwined spiral solvent channel is driven by weak C–Cl…O and C–H…N interactions based on extraordinary parallel spirals which were structured from supramolecular synthon macrocycle 1（C44H44N4O4） with a propargylamine backbone. The product is characterized by ^1H NMR, ^13C NMR, IR and HRMS, and further confirmed by single-crystal X-ray diffraction. It crystallizes in the monoclinic system, space group C2/c, with a = 28.922（3）, b = 8.5069（9）, c = 21.687（2）A^°, β = 130.6320（10）°, V = 4049.4（7） A^°3 and Z = 8. A total of 11874 reflections were collected, of which 4942 were independent（Rint = 0.0590） and 2937 were observed with I 〉 2σ（I）. The final full-matrix least-squares refinement gave R（I 〉 2s（I）） = 0.069 and w R = 0.167, S = 1.05,（Δρ）max = 0.20 and（Δρ）min =-0.22 e·A^1-3. The fluorescence of the product is discussed.
基金supported by the National Natural Science Foundation of China(21004024)the Province Natural Science Foundation of Fujian,China(2011J01046)+2 种基金the Program for New Century Excellent Talents in University of Fujian Province(2012FJ-NCET-ZR03)the University Distinguished Young Research Talent Training Program of Fujian Province(11FJPY02)the Promotion Program for Young and Middle-aged Teacher in Scienceand Technology Research of Huaqiao University(ZQN-YX103)~~
基金supported by the National Natural Science Foundation of China(Nos.21601121,21305086)the Natural Science Foundation of Shanghai(No.18ZR1416400)+1 种基金support of the Shanghai University of Engineering Science(Nos.201810856017,A1-0601-19-01017)the Opening Project of Shanghai Key Laboratory of Chemical Biology for financial support。
文摘Highly active and stable magnetic copper catalysts were successfully achieved by magnetic induced Stober method and subsequent hydrothermal reaction with copper ions in alkaline condition.The high content of Cu2+as well as the unique structures of hierarchical copper silicate in the as-prepared catalysts endowed their outstanding catalytic performance.Efficient decarboxylative A3-coupling of a-keto acid,amine and alkyne was realized with the low Fe3 O4@CuSiO3 loading.A range of propargylamines were produced in good to excellent yields under solvent-free condition.Moreover,the catalyst can be easily separated from the final organic product with an external magnet.Also,this kind of catalyst could be recycled up to six times while maintaining its activity.
基金financial support from the National Natural Science Foundation of China (Nos. 21802093, 21536003)Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi (No. 2019L0408)the Ph D Start-up Foundation of Shanxi Medical University (No. 03201501) for the financial support。
文摘Several simple, fast and practical protocols have been developed to synthesize internal or terminal propargylamines and chalcones via A^(3)-coupling reaction of aldehydes, amines, and alkynes catalyzed by an easily available catalyst Ag_(2)CO_(3)under solvent-free condition. The reaction proceeded smoothly to deliver various products in good-to-excellent yields with good functional group tolerance. Gram-scale preparation, bioactive molecule synthesis and asymmetric substrates have been demonstrated. Furthermore,plausible mechanisms for the synthesis of different products have been proposed.
