Zwitterionic palladium complexes

Room-temperature Suzuki-Miyaura cross-coupling of sterically hindered substrates in an aqueous medium

Jhen Yi Lee, Dabalina Ghosh, Jing Yi Lee, Shih Sheng Wu, Ching-Han Hu, Shuang De Liu, Hon Man Lee

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

A series of new imidazolium chlorides were straightforwardly prepared from the reactions between chloroacetone and imidazole derivatives. Deprotonation of the methylene proton next to the ketone group in these salts by pyridine led to the formation of a monodentate ligand that coordinated to palladium, readily forming zwitterionic anionic palladium pyridine complexes bearing a formal positive charge on the ligand ancillary. The pyridine ligand in the zwitterionic complexes can be facilely replaced by phosphine ligands. Seven of these new complexes were successfully characterized by X-ray crystallography. The zwitterionic phosphine complexes were highly efficient in catalyzing room-temperature Suzuki-Miyaura reactions between sterically hindered aryl chlorides and arylboronic acids in an aqueous medium.

Original languageEnglish
Pages (from-to)6481-6492
Number of pages12
JournalOrganometallics
Volume33
Issue number22
DOIs
Publication statusPublished - 2014 Nov 24

Fingerprint

phosphine
cross coupling
Palladium
palladium
Ligands
pyridines
ligands
room temperature
Substrates
phosphines
Bearings (structural)
chlorides
Temperature
Deprotonation
X ray crystallography
Ketones
imidazoles
methylene
ketones
crystallography

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Lee, Jhen Yi ; Ghosh, Dabalina ; Lee, Jing Yi ; Wu, Shih Sheng ; Hu, Ching-Han ; Liu, Shuang De ; Lee, Hon Man. / Zwitterionic palladium complexes : Room-temperature Suzuki-Miyaura cross-coupling of sterically hindered substrates in an aqueous medium. In: Organometallics. 2014 ; Vol. 33, No. 22. pp. 6481-6492.
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Zwitterionic palladium complexes : Room-temperature Suzuki-Miyaura cross-coupling of sterically hindered substrates in an aqueous medium. / Lee, Jhen Yi; Ghosh, Dabalina; Lee, Jing Yi; Wu, Shih Sheng; Hu, Ching-Han; Liu, Shuang De; Lee, Hon Man.

In: Organometallics, Vol. 33, No. 22, 24.11.2014, p. 6481-6492.

Research output: Contribution to journalArticle

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AU - Lee, Jhen Yi

AU - Ghosh, Dabalina

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AU - Wu, Shih Sheng

AU - Hu, Ching-Han

AU - Liu, Shuang De

AU - Lee, Hon Man

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