A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to β,β-Disubstituted Enones

Heintz, Patrick M.; Schumacher, Brian P.; Chen, Minda; Huang, Wenyu; Stanley, Levi M.

doi:10.1002/cctc.201900894

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:

Heintz, Patrick M. ^[1]; Schumacher, Brian P. ^[2]; Chen, Minda ^[1]; Huang, Wenyu ^[1];

^[2]

Ames Lab. and Iowa State Univ., Ames, IA (United States)
Iowa State Univ., Ames, IA (United States)

Publication Date:: 2019-06-25

Research Org.:: Ames Lab., 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:https://doi.org/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:https://doi.org/10.1002/cctc.201900894.  https://www.osti.gov/servlets/purl/1557818.

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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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DOI: https://doi.org/10.1002/cctc.201900894

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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

Citation Formats

Salen-Based Covalent Organic Framework journal, April 2017

Homochiral 2D Porous Covalent Organic Frameworks for Heterogeneous Asymmetric Catalysis journal, September 2016

Constructing Crystalline Covalent Organic Frameworks from Chiral Building Blocks journal, September 2016

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Highly Stable Keto-Enamine Salicylideneanilines journal, October 2003

Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones in Aqueous Media: Formation of Bis-benzylic and ortho -Substituted Benzylic Quaternary Centers journal, August 2015

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journal, August 2015

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journal, August 2018

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