Synthesis of Tridentate [1,2,4] Triazinyl-Pyridin-2-yl Indole Lewis Basic Complexants via Pd-Catalyzed Suzuki–Miyaura Cross-Coupling
Abstract
Full closure of the nuclear fuel cycle is predicated, in part, on defining efficient separations processes for the effective speciation of the neutron-absorbing lanthanides from the minor actinides post-PUREX. Pursuant to the aforementioned, a class of tridentate, Lewis basic procomplexants have been prepared leveraging a Pd-catalyzed Suzuki–Miyaura cross-coupling between 6-bromo-[1,2,4]-triazinylpyridine derivatives and various protected indole-boronic acids to afford functionalized 2-[6-(5,6-diphenyl-[1,2,4]triazin-3-yl)-pyridin-2-yl]-1H-indoles. A highly active catalyst/ligand system with low loadings was employed rapidly affording 26 examples in yields as high as 85%. Method optimization, substrate and indole scope, comparative analysis between coupling reagents, and a scale-up experiment are reported.
- Publication Date:
- Research Org.:
- Tennessee Technological Univ., Cookeville, TN (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22); National Science Foundation (NSF)
- OSTI Identifier:
- 1572218
- Alternate Identifier(s):
- OSTI ID: 1574459
- Grant/Contract Number:
- SC0018033
- Resource Type:
- Published Article
- Journal Name:
- ACS Omega
- Additional Journal Information:
- Journal Volume: 4; Journal Issue: 20; Journal ID: ISSN 2470-1343
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Gulledge, Zachary Z., Tedder, Mariah L., Lyons, Kyle R., and Carrick, Jesse D. Synthesis of Tridentate [1,2,4] Triazinyl-Pyridin-2-yl Indole Lewis Basic Complexants via Pd-Catalyzed Suzuki–Miyaura Cross-Coupling. United States: N. p., 2019.
Web. doi:10.1021/acsomega.9b02891.
Gulledge, Zachary Z., Tedder, Mariah L., Lyons, Kyle R., & Carrick, Jesse D. Synthesis of Tridentate [1,2,4] Triazinyl-Pyridin-2-yl Indole Lewis Basic Complexants via Pd-Catalyzed Suzuki–Miyaura Cross-Coupling. United States. doi:10.1021/acsomega.9b02891.
Gulledge, Zachary Z., Tedder, Mariah L., Lyons, Kyle R., and Carrick, Jesse D. Tue .
"Synthesis of Tridentate [1,2,4] Triazinyl-Pyridin-2-yl Indole Lewis Basic Complexants via Pd-Catalyzed Suzuki–Miyaura Cross-Coupling". United States. doi:10.1021/acsomega.9b02891.
@article{osti_1572218,
title = {Synthesis of Tridentate [1,2,4] Triazinyl-Pyridin-2-yl Indole Lewis Basic Complexants via Pd-Catalyzed Suzuki–Miyaura Cross-Coupling},
author = {Gulledge, Zachary Z. and Tedder, Mariah L. and Lyons, Kyle R. and Carrick, Jesse D.},
abstractNote = {Full closure of the nuclear fuel cycle is predicated, in part, on defining efficient separations processes for the effective speciation of the neutron-absorbing lanthanides from the minor actinides post-PUREX. Pursuant to the aforementioned, a class of tridentate, Lewis basic procomplexants have been prepared leveraging a Pd-catalyzed Suzuki–Miyaura cross-coupling between 6-bromo-[1,2,4]-triazinylpyridine derivatives and various protected indole-boronic acids to afford functionalized 2-[6-(5,6-diphenyl-[1,2,4]triazin-3-yl)-pyridin-2-yl]-1H-indoles. A highly active catalyst/ligand system with low loadings was employed rapidly affording 26 examples in yields as high as 85%. Method optimization, substrate and indole scope, comparative analysis between coupling reagents, and a scale-up experiment are reported.},
doi = {10.1021/acsomega.9b02891},
journal = {ACS Omega},
number = 20,
volume = 4,
place = {United States},
year = {2019},
month = {10}
}
DOI: 10.1021/acsomega.9b02891
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