Optimization of Sodium-Catalyzed Si–N Bond Formation Through a Comparative Study of Group 1 Alkoxides
- 1Department of Chemistry, University of Vermont, 82 University Place, Burlington, Vermont, USA, 05405
- 2Gund Institute for Environment, Farrell Hall, 210 Colchester Avenue, Burlington, Vermont, USA, 05405
Abstract
A systematic comparison of group 1 tert-amylate (OtAmyl) salts as precatalysts for Si–N heterodehydrocoupling is reported with a focus on NatOAmyl. The heavier alkali metals provide good to excellent conversions with all substrates screened, including tertiary silanes and secondary amines, which are challenging substrates in prior literature reports. Although the activity of NatOAmyl is limited in comparison to rubidium and cesium congeners, this can be improved with judicious solvent choice, particularly DMSO. The overall findings support that a single inexpensive and sustainable catalyst can be primarily used for Si–N bond formation; however, if the substrates are particularly challenging, CstOAmyl will provide high conversion. This analysis provides a systematic approach for pragmatic catalysts to engage in bond formation with abundant silicon and nitrogen that serves synthesis and materials chemistry.
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BibTeX
@misc{iyanda2026optimization,
title = {{Optimization of Sodium-Catalyzed Si–N Bond Formation Through a Comparative Study of Group 1 Alkoxides}},
author = {Shakira A. Iyanda and Rory A. Wells and Gwyneth A. Oden and Rory Waterman},
howpublished = {ChemRxiv},
year = {2026},
month = oct,
doi = {10.26434/chemrxiv.15010143/v1},
url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010143/v1},
note = {CC BY-NC-ND},
}
RIS
TY - UNPB
TI - Optimization of Sodium-Catalyzed Si–N Bond Formation Through a Comparative Study of Group 1 Alkoxides
AU - Shakira A. Iyanda
AU - Rory A. Wells
AU - Gwyneth A. Oden
AU - Rory Waterman
PY - 2026
DA - 2026/10/09
PB - ChemRxiv
DO - 10.26434/chemrxiv.15010143/v1
UR - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010143/v1
AB - A systematic comparison of group 1 tert-amylate (OtAmyl) salts as precatalysts for Si–N heterodehydrocoupling is reported with a focus on NatOAmyl. The heavier alkali metals provide good to excellent conversions with all substrates screened, including tertiary silanes and secondary amines, which are challenging substrates in prior literature reports. Although the activity of NatOAmyl is limited in comparison to rubidium and cesium congeners, this can be improved with judicious solvent choice, particularly DMSO. The overall findings support that a single inexpensive and sustainable catalyst can be primarily used for Si–N bond formation; however, if the substrates are particularly challenging, CstOAmyl will provide high conversion. This analysis provides a systematic approach for pragmatic catalysts to engage in bond formation with abundant silicon and nitrogen that serves synthesis and materials chemistry.
ER -