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Article
A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to beta,beta-Disubstituted Enones
Ames Laboratory Accepted Manuscripts
  • Patrick M. Heintz, Iowa State University and Ames Laboratory
  • Brian P. Schumacher, Iowa State University
  • Minda Chen, Iowa State University and Ames Laboratory
  • Wenyu Huang, Iowa State University and Ames Laboratory
  • Levi M. Stanley, Iowa State University
Publication Date
9-5-2019
Department
Ames Laboratory; Chemistry
OSTI ID+
1557818
Report Number
IS-J 10004
DOI
10.1002/cctc.201900894
Journal Title
ChemCatChem
Abstract

A palladium(II)-functionalized covalent organic framework (Pd@TpBpy COF) constructed 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 beta,beta-disubstituted enones form a variety of ketones containing benzylic all-carbon quaternary centers in up to 92 % isolated yield. Studies on the recyclability of Pd@TpBpy COF show this catalyst remains active through at least 7 cycles and shows superior stability to related MOF catalysts with bipyridine linker units.

DOE Contract Number(s)
AC02-07CH11358
Language
en
Publisher
Iowa State University Digital Repository, Ames IA (United States)
Disciplines
Citation Information
Patrick M. Heintz, Brian P. Schumacher, Minda Chen, Wenyu Huang, et al.. "A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to beta,beta-Disubstituted Enones" Vol. 11 Iss. 17 (2019) p. 4286 - 4290
Available at: http://works.bepress.com/wenyu_huang/62/