Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates
Abstract
A strategy for the direct functionalization strategy of inertial dialkyl phosphonates with hydroxy compounds to afford diverse mixed phosphonates with good yields and functional-group tolerance has been developed. Additionally, mechanistic investigations involving both NMR studies and DFT studies suggest that an unprecedented highly reactive PV species (phosphoryl pyridin-1-ium salt), a key intermediate for this new synthetic transformation, is generated in situ from dialkyl phosphonate in the presence of Tf2O/pyridine.
- Authors:
-
[2];
[2];
[1]
- Univ. of Nevada, Las Vegas, NV (United States). Dept. of Chemistry and Biochemistry
- Univ. of Colorado, Denver, CO (United States). Dept. of Chemistry
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC); Univ. of California, Oakland, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC)
- OSTI Identifier:
- 1543471
- Grant/Contract Number:
- AC02-05CH11231
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Angewandte Chemie (International Edition)
- Additional Journal Information:
- Journal Name: Angewandte Chemie (International Edition); Journal Volume: 57; Journal Issue: 22; Journal ID: ISSN 1433-7851
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; chemistry; alkyloxylation; aryloxylation; DFT study; phosphates; phosphoryl pyridin-1-ium
Citation Formats
Huang, Hai, Denne, Johanna, Yang, Chou-Hsun, Wang, Haobin, and Kang, Jun Yong. Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates. United States: N. p., 2018.
Web. doi:10.1002/anie.201802082.
Huang, Hai, Denne, Johanna, Yang, Chou-Hsun, Wang, Haobin, & Kang, Jun Yong. Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates. United States. https://doi.org/10.1002/anie.201802082
Huang, Hai, Denne, Johanna, Yang, Chou-Hsun, Wang, Haobin, and Kang, Jun Yong. Mon .
"Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates". United States. https://doi.org/10.1002/anie.201802082. https://www.osti.gov/servlets/purl/1543471.
@article{osti_1543471,
title = {Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates},
author = {Huang, Hai and Denne, Johanna and Yang, Chou-Hsun and Wang, Haobin and Kang, Jun Yong},
abstractNote = {A strategy for the direct functionalization strategy of inertial dialkyl phosphonates with hydroxy compounds to afford diverse mixed phosphonates with good yields and functional-group tolerance has been developed. Additionally, mechanistic investigations involving both NMR studies and DFT studies suggest that an unprecedented highly reactive PV species (phosphoryl pyridin-1-ium salt), a key intermediate for this new synthetic transformation, is generated in situ from dialkyl phosphonate in the presence of Tf2O/pyridine.},
doi = {10.1002/anie.201802082},
journal = {Angewandte Chemie (International Edition)},
number = 22,
volume = 57,
place = {United States},
year = {Mon Apr 16 00:00:00 EDT 2018},
month = {Mon Apr 16 00:00:00 EDT 2018}
}
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Figure 1: Examples of pharmaceutically-relevant mixed alkyl aryl phosphonates
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