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

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2019-09-05
Authors
Schumacher, Brian
Chen, Minda
Huang, Wenyu
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Stanley, Levi
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Huang, Wenyu
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Ames National Laboratory

Ames National Laboratory is a government-owned, contractor-operated national laboratory of the U.S. Department of Energy (DOE), operated by and located on the campus of Iowa State University in Ames, Iowa.

For more than 70 years, the Ames National Laboratory has successfully partnered with Iowa State University, and is unique among the 17 DOE laboratories in that it is physically located on the campus of a major research university. Many of the scientists and administrators at the Laboratory also hold faculty positions at the University and the Laboratory has access to both undergraduate and graduate student talent.

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Chemistry

The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).

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The Department of Chemistry was founded in 1880.

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1880-present

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Ames National LaboratoryChemistry
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.

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