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

Journal Article · Tue Jun 25 00:00:00 EDT 2019 · ChemCatChem

DOI:https://doi.org/10.1002/cctc.201900894· OSTI ID:1557818

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)

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.

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Research Organization:: Ames Laboratory (AMES), Ames, IA (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-07CH11358

OSTI ID:: 1557818

Alternate ID(s):: OSTI ID: 1547943

Report Number(s):: IS-J-10004

Journal Information:: ChemCatChem, Vol. 11, Issue 17; ISSN 1867-3880

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 12 works

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
covalent organic framework (COF)
conjugate addition
palladium
quaternary centers
heterogeneous catalysis

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

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