IPr **(4‑Bp) Highly Hindered, Ring Extended N‑Heterocyclic Carbenes
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| Title: | IPr **(4‑Bp) Highly Hindered, Ring Extended N‑Heterocyclic Carbenes |
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| Authors: | Yuzhuo Sha, Wenchao Chu, Roger Lalancette, Roman Szostak, Michal Szostak |
| Publication Year: | 2025 |
| Subject Terms: | Biophysics, Biochemistry, Genetics, Pharmacology, Biotechnology, Ecology, Inorganic Chemistry, Chemical Sciences not elsewhere classified, Information Systems not elsewhere classified, square planar geometry, heterocyclic carbenes due, found broad utilization, extended biphenyl wingtip, easily accessible n, diphenylmethyl )- 4, bear biphenyl wingtips, heterocyclic carbene ligands, demonstrates steric flexibility, ipr **< sup, sterically hindered n, meo , bur , ipr, sterically flexible ligand, study demonstrates, sterically bulky, sterically bulkier, highly hindered, including ipr, ylidene ligands |
| Description: | There is a strong demand for the development of sterically hindered N-heterocyclic carbenes due to their potential to stabilize reactive organometallic species. IPr* (IPr* = 1,3-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)imidazo-2-ylidene) is a highly hindered and sterically flexible ligand, which has found broad utilization in coordination chemistry. Herein, we report the synthesis, structural, and electronic characterization of IPr** (4‑Bp) a class of novel, sterically bulky, and easily accessible N-heterocyclic carbene ligands that bear biphenyl wingtips. Coordination chemistry to Ag(I), Cu(I), and Pd(II) is presented. The biphenyl wingtip permits extension of the %V bur of IPr** (4‑Bp) to 58.8%, linear geometry, which is the highest reported to date for imidazol-2-ylidene ligands. The synthesis of an electron-rich congener, IPr** MeO(4‑Bp) , which is analogous to the popular IPr* MeO ligand, is also presented. Coordination to Pd(II) demonstrates steric flexibility, where the %V bur changes to 42.8% for square planar geometry. The study demonstrates that IPr **(4‑Bp) with an extended biphenyl wingtip is sterically bulkier than common imidazol-2-ylidenes, including IPr, IPr*, IPr # , and IPr* (2‑Np) . Considering the essential role of sterically hindered N-heterocyclic carbene ligands in various areas of coordination chemistry and metal catalysis, this new class of NHCs is poised for rapid and widespread application. |
| Document Type: | article in journal/newspaper |
| Language: | unknown |
| Relation: | https://figshare.com/articles/journal_contribution/IPr_sup_4_Bp_sup_Highly_Hindered_Ring_Extended_N_Heterocyclic_Carbenes/29858623 |
| DOI: | 10.1021/acs.organomet.5c00232.s001 |
| Availability: | https://doi.org/10.1021/acs.organomet.5c00232.s001 https://figshare.com/articles/journal_contribution/IPr_sup_4_Bp_sup_Highly_Hindered_Ring_Extended_N_Heterocyclic_Carbenes/29858623 |
| Rights: | CC BY-NC 4.0 |
| Accession Number: | edsbas.32B6078B |
| Database: | BASE |
Nájsť tento článok vo Web of Science | Abstract: | There is a strong demand for the development of sterically hindered N-heterocyclic carbenes due to their potential to stabilize reactive organometallic species. IPr* (IPr* = 1,3-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)imidazo-2-ylidene) is a highly hindered and sterically flexible ligand, which has found broad utilization in coordination chemistry. Herein, we report the synthesis, structural, and electronic characterization of IPr** (4‑Bp) a class of novel, sterically bulky, and easily accessible N-heterocyclic carbene ligands that bear biphenyl wingtips. Coordination chemistry to Ag(I), Cu(I), and Pd(II) is presented. The biphenyl wingtip permits extension of the %V bur of IPr** (4‑Bp) to 58.8%, linear geometry, which is the highest reported to date for imidazol-2-ylidene ligands. The synthesis of an electron-rich congener, IPr** MeO(4‑Bp) , which is analogous to the popular IPr* MeO ligand, is also presented. Coordination to Pd(II) demonstrates steric flexibility, where the %V bur changes to 42.8% for square planar geometry. The study demonstrates that IPr **(4‑Bp) with an extended biphenyl wingtip is sterically bulkier than common imidazol-2-ylidenes, including IPr, IPr*, IPr # , and IPr* (2‑Np) . Considering the essential role of sterically hindered N-heterocyclic carbene ligands in various areas of coordination chemistry and metal catalysis, this new class of NHCs is poised for rapid and widespread application. |
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| DOI: | 10.1021/acs.organomet.5c00232.s001 |