journal article·2024-07Open access

Oxime Palladacycle Supported on Magnetic Meoporous Silica: An Efficient Catalyst for Copper‐Free Acyl Sonogashira Reaction

Fatemeh Ghahramani, Yagoub Mansoori, Michael John

ChemNanoMat· Volume 10· Issue 7

Abstract

Abstract The catalytic activity of the supported bis(oxime palladacycle) catalyst was evaluated in the acyl Sonogashira reaction. The reaction conditions, such as solvent, base, and palladium content, were screened to achieve the best catalytic performance. Tetrahydrofuran (THF) solvent, triethylamine (Et3N) base, and the reaction temperature of 110 °C were found to be ideal for achieving high yields of the desired products. Furthermore, a catalyst loading of only 0.22 mol% palladium was sufficient to achieve good conversion. Broad ranges of aryl acetylenes and benzoyl chlorides were successfully coupled to give the desired acetylenic ketones. The reaction appeared to proceed efficiently using a small amount of catalyst. The magnetic property of the catalyst allowed for easy separation using an external magnet. The catalyst was stable and reused for multiple reaction runs without a significant deactivation. After seven cycles, the catalyst maintained over 90 % of its initial catalytic activity.
Source: crossref · Quality: baseline

Research context

OpenAlex topics: Catalytic Cross-Coupling Reactions · Chemical Synthesis and Reactions · Asymmetric Hydrogenation and Catalysis

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Department of Applied Chemistry Faculty of Science University of Mohaghegh Ardabili Daneshgah St. Ardabil Iran 56199-11367 Tel

Nanoscience and Nanotechnology Research Group University of Mohaghegh Ardabili Ardabil Iran 56199-11367

Georg-August-Universität Göttingen Institut für Anorganische Chemie Tammannstrasse 4 37077 Göttingen Germany

Funding

University of Mohaghegh Ardabili

References (90)

Show source-provided references
1.
2. 10.1021/cr990304810.1021/cr9903048 ↗
3. 10.1002/anie.20170169010.1002/anie.201701690 ↗
4.
5. 10.1002/ejoc.20170007610.1002/ejoc.201700076 ↗
6. 10.1021/acsomega.8b0288610.1021/acsomega.8b02886 ↗
7. 10.1021/ol036338q10.1021/ol036338q ↗
8. 10.1039/b700838d10.1039/b700838d ↗
9. 10.1007/s00044-019-02314-810.1007/s00044-019-02314-8 ↗
10. 10.1021/om400758b10.1021/om400758b ↗
11. 10.1016/j.molstruc.2013.09.04310.1016/j.molstruc.2013.09.043 ↗
12. 10.1039/C5RA23759A10.1039/C5RA23759A ↗
13. 10.1021/acs.chemrev.9b0027710.1021/acs.chemrev.9b00277 ↗
14. 10.1021/om700891k10.1021/om700891k ↗
15.
16. 10.1021/jacs.1c0603610.1021/jacs.1c06036 ↗
17. 10.1021/acsomega.3c0117910.1021/acsomega.3c01179 ↗
18. 10.1021/acs.joc.2c0138610.1021/acs.joc.2c01386 ↗
19. 10.1002/anie.20230334510.1002/anie.202303345 ↗
20. 10.3390/molecules2811436410.3390/molecules28114364 ↗
21. 10.1055/s-1977-2457410.1055/s-1977-24574 ↗
22.
23. 10.1002/ejic.20080015710.1002/ejic.200800157 ↗
24. 10.1002/chem.20090290610.1002/chem.200902906 ↗
25. 10.1016/j.tetlet.2012.01.10510.1016/j.tetlet.2012.01.105 ↗
26. 10.1039/C6OB00483K10.1039/C6OB00483K ↗
27. 10.1007/s10562-020-03235-710.1007/s10562-020-03235-7 ↗
28. 10.1021/acscatal.2c0620510.1021/acscatal.2c06205 ↗
29. 10.1081/SCC-10010604510.1081/SCC-100106045 ↗
30. 10.1002/hlca.20089003210.1002/hlca.200890032 ↗
31. 10.1016/j.tet.2009.10.03110.1016/j.tet.2009.10.031 ↗
32. 10.1016/j.jorganchem.2009.09.03610.1016/j.jorganchem.2009.09.036 ↗
33.
34. 10.1039/c1gc15869d10.1039/c1gc15869d ↗
35. 10.1055/s-0030-125932210.1055/s-0030-1259322 ↗
36. 10.1039/c3nj00425b10.1039/c3nj00425b ↗
37. 10.1002/slct.20170115010.1002/slct.201701150 ↗
38. 10.3390/catal1010118610.3390/catal10101186 ↗
39. 10.1002/slct.20200110610.1002/slct.202001106 ↗
40. 10.1007/s10562-019-02959-510.1007/s10562-019-02959-5 ↗
41. 10.1007/s40995-021-01156-710.1007/s40995-021-01156-7 ↗
42.
43. 10.1021/jacs.3c1304410.1021/jacs.3c13044 ↗
44. 10.1055/s-0043-177317110.1055/s-0043-1773171 ↗
45.
46. 10.1021/ja01006a01210.1021/ja01006a012 ↗
47. 10.1021/ja01092a06310.1021/ja01092a063 ↗
48. 10.1246/bcsj.43.348010.1246/bcsj.43.3480 ↗
49. 10.1016/j.ccr.2014.07.01910.1016/j.ccr.2014.07.019 ↗
50.
51. 10.1016/j.jorganchem.2004.07.05410.1016/j.jorganchem.2004.07.054 ↗
52. 10.1002/cctc.20160003510.1002/cctc.201600035 ↗
53. 10.1021/jo025619t10.1021/jo025619t ↗
54. 10.1002/adsc.20030306710.1002/adsc.200303067 ↗
55. 10.1002/adsc.20050549410.1002/adsc.200505494 ↗
56. 10.1021/jo202482h10.1021/jo202482h ↗
57. 10.1016/j.tet.2013.01.04910.1016/j.tet.2013.01.049 ↗
58. 10.1016/j.ica.2018.08.04310.1016/j.ica.2018.08.043 ↗
59. 10.1002/aoc.509810.1002/aoc.5098 ↗
60. 10.1080/00397911.2020.182696910.1080/00397911.2020.1826969 ↗
61. 10.1002/adsc.20070030110.1002/adsc.200700301 ↗
62. 10.1039/C5CY00413F10.1039/C5CY00413F ↗
63. 10.1021/acs.orglett.5b0059410.1021/acs.orglett.5b00594 ↗
64. 10.1002/slct.20160126610.1002/slct.201601266 ↗
65. 10.1039/b004412l10.1039/b004412l ↗
66. 10.1007/s10563-023-09396-w10.1007/s10563-023-09396-w ↗
67. 10.1039/b211742h10.1039/b211742h ↗
68.
69. 10.1016/j.cej.2014.10.03510.1016/j.cej.2014.10.035 ↗
70. 10.1016/j.jorganchem.2023.12272410.1016/j.jorganchem.2023.122724 ↗
71. 10.1002/pat.430710.1002/pat.4307 ↗
72.
73. 10.1039/C5RA23760B10.1039/C5RA23760B ↗
74. 10.1039/C9SE00015A10.1039/C9SE00015A ↗
75. 10.1002/cctc.20130074210.1002/cctc.201300742 ↗
76. 10.1016/j.scitotenv.2018.01.05710.1016/j.scitotenv.2018.01.057 ↗
77. 10.1016/j.mcat.2018.12.00710.1016/j.mcat.2018.12.007 ↗
78. 10.3390/catal703009410.3390/catal7030094 ↗
79.
80. W. L. F. Armarego C. L. L. Chai Purification of laboratory chemicals 5thed. Butterworth-Heinemann Burlington 2003;10.1016/B978-075067571-0/50008-9 ↗
81. Ghahramani F. · Catal. Surv. Asia · 2023
82. 10.1126/science.279.5350.54810.1126/science.279.5350.548 ↗
83. 10.1351/pac19855704060310.1351/pac198557040603 ↗
84. 10.1021/jp800363s10.1021/jp800363s ↗
85. 10.1002/slct.20210212410.1002/slct.202102124 ↗
86. 10.1039/C7NJ01376K10.1039/C7NJ01376K ↗
87. 10.1021/jm049939b10.1021/jm049939b ↗
88. 10.1021/ie501305x10.1021/ie501305x ↗
89. 10.1039/C5OB00502G10.1039/C5OB00502G ↗
90. 10.1039/D1CC07018E10.1039/D1CC07018E ↗