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

Journal Article · · ChemCatChem
 [1];  [2];  [1];  [1]; ORCiD logo [2]
  1. Ames Lab. and Iowa State Univ., Ames, IA (United States)
  2. Iowa State Univ., Ames, IA (United States)
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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.

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

References (31)

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Figures / Tables (7)

Scheme 1(p. 1)figure Scheme 1
Table 1(p. 2)table Table 1
Figure 1(p. 3)figure Figure 1
Scheme 2(p. 3)figure Scheme 2
Figure 2(p. 4)figure Figure 2
Figure 3(p. 5)figure Figure 3
Figure 4(p. 5)figure Figure 4

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