1, 2, 3-Triazole framework: a strategic structure for C–H⋯X hydrogen bonding and practical design of an effective Pd-catalyst for carbonylation and carbon–carbon bond formation. Issue 34 (11th June 2021)

• Record Type: Journal Article
• Authors: Mohammadsaleh, Fatemeh; Jahromi, Maryam Dehdashti; Hajipour, Abdol Reza; Hosseini, Seyed Mostafa; Niknam, Khodabakhsh
• Is Part Of: RSC advances. Volume 11:Issue 34(2021)
• Page Start: 20812
• Page End: 20823
• Publication Date: 2021-06-11
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1ra03356e
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : The C–H hydrogen bonding of a 1, 2, 3-triazole framework was studied. An Fe3 O4 –chitosan core–shell incorporating a triazole/Pd complex was investigated as a nanocatalyst in carbonylation and C–C coupling. Abstract : 1, 2, 3-Triazole is an interesting N-heterocyclic framework which can act as both a hydrogen bond donor and metal chelator. In the present study, C–H hydrogen bonding of the 1, 2, 3-triazole ring was surveyed theoretically and the results showed a good agreement with the experimental observations. The click-modified magnetic nanocatalyst Pd@click-Fe3 O4 /chitosan was successfully prepared, in which the triazole moiety plays a dual role as both a strong linker and an excellent ligand and immobilizes the palladium species in the catalyst matrix. This nanostructure was well characterized and found to be an efficient catalyst for the CO gas-free formylation of aryl halides using formic acid (HCOOH) as the most convenient, inexpensive and environmentally friendly CO source. Here, the aryl halides are selectively converted to the corresponding aromatic aldehydes under mild reaction conditions and low Pd loading. The activity of this catalyst was also excellent in the Suzuki cross-coupling reaction of various aryl halides with phenylboronic acids in EtOH/H2 O (1 : 1) at room temperature. In addition, this catalyst was stable in the reaction media and could be magnetically separated and recovered several times.