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Title: 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:
 [1];  [2];  [1];  [1]; ORCiD logo [2]
+ Show Author Affiliations
  1. Ames Lab. and Iowa State Univ., Ames, IA (United States)
  2. 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.
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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. doi:10.1002/cctc.201900894.
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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. doi:10.1002/cctc.201900894.
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@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 = {2019},
month = {6}
}
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Journal Article:
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This content will become publicly available on June 25, 2020
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DOI:  10.1002/cctc.201900894
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