A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to β,β-Disubstituted Enones
Abstract
A palladium(II)-functionalized covalent organic framework (Pd@TpBpy COF) built from 1,3,5-triformylphloroglucinol (Tp) and [2,2'-bipyridine]-5,5'-diamine (Bpy) is reported as a recyclable catalyst for conjugate additions in aqueous media. Additions of an array of stereoelectronically diverse arylboronic acid nucleophiles to β,β-disubstituted enones form a variety of ketones containing benzylic all-carbon quaternary centers in up to 92 % isolated yield. Research on the recyclability of Pd@TpBpy COF demonstrate this catalyst remains active through at least 7 cycles and shows superior stability to related MOF catalysts with bipyridine linker units.
- Authors:
-
[2]
- Ames Lab. and Iowa State Univ., Ames, IA (United States)
- Iowa State Univ., Ames, IA (United States)
- Publication Date:
- Research Org.:
- Ames Laboratory (AMES), Ames, IA (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1557818
- Alternate Identifier(s):
- OSTI ID: 1547943
- Report Number(s):
- IS-J-10004
Journal ID: ISSN 1867-3880
- Grant/Contract Number:
- AC02-07CH11358
- Resource Type:
- Accepted Manuscript
- Journal Name:
- ChemCatChem
- Additional Journal Information:
- Journal Volume: 11; Journal Issue: 17; Journal ID: ISSN 1867-3880
- Publisher:
- ChemPubSoc Europe
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; covalent organic framework (COF); conjugate addition; palladium; quaternary centers; heterogeneous catalysis
Citation Formats
Heintz, Patrick M., Schumacher, Brian P., Chen, Minda, Huang, Wenyu, and Stanley, Levi M. A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to β,β-Disubstituted Enones. United States: N. p., 2019.
Web. doi:10.1002/cctc.201900894.
Heintz, Patrick M., Schumacher, Brian P., Chen, Minda, Huang, Wenyu, & Stanley, Levi M. A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to β,β-Disubstituted Enones. United States. https://doi.org/10.1002/cctc.201900894
Heintz, Patrick M., Schumacher, Brian P., Chen, Minda, Huang, Wenyu, and Stanley, Levi M. Tue .
"A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to β,β-Disubstituted Enones". United States. https://doi.org/10.1002/cctc.201900894. https://www.osti.gov/servlets/purl/1557818.
@article{osti_1557818,
title = {A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to β,β-Disubstituted Enones},
author = {Heintz, Patrick M. and Schumacher, Brian P. and Chen, Minda and Huang, Wenyu and Stanley, Levi M.},
abstractNote = {A palladium(II)-functionalized covalent organic framework (Pd@TpBpy COF) built from 1,3,5-triformylphloroglucinol (Tp) and [2,2'-bipyridine]-5,5'-diamine (Bpy) is reported as a recyclable catalyst for conjugate additions in aqueous media. Additions of an array of stereoelectronically diverse arylboronic acid nucleophiles to β,β-disubstituted enones form a variety of ketones containing benzylic all-carbon quaternary centers in up to 92 % isolated yield. Research on the recyclability of Pd@TpBpy COF demonstrate this catalyst remains active through at least 7 cycles and shows superior stability to related MOF catalysts with bipyridine linker units.},
doi = {10.1002/cctc.201900894},
journal = {ChemCatChem},
number = 17,
volume = 11,
place = {United States},
year = {Tue Jun 25 00:00:00 EDT 2019},
month = {Tue Jun 25 00:00:00 EDT 2019}
}
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Cited by: 12 works
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Figures / Tables:
Scheme 1: a) Binding of Pd(II) in Pd@TpBpy COF. b) Conjugate Additions to Form Benzylic All-Carbon Quaternary Centers Catalyzed by Pd@TpBpy COF.
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Figures / Tables found in this record:
Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.