Well-defined palladium(0) complexes bearing N-heterocyclic carbene and phosphine moieties

Efficient catalytic applications in the Mizoroki-Heck reaction and direct C-H functionalization

Jhen Yi Lee, Jiun Shian Shen, Ru Jiun Tzeng, I. Chen Lu, Jenn Huei Lii, Ching-Han Hu, Hon Man Lee

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Two series of well-defined palladium(0) complexes with phosphine-functionalized N-heterocyclic carbene ligands were prepared. These complexes featured six- and seven-membered chelate rings in the two series. Among the seven-membered chelate complexes, those featuring the PCy2 moiety exhibited observable fluxional behavior on the NMR time scale, corresponding to the interchange between two sets of conformations. Most of these novel complexes were successfully structurally characterized by single-crystal X-ray diffraction studies. These two series of palladium(0) complexes were tested for their potential catalytic applications in two mechanistically distinct reactions, namely, Mizoroki-Heck coupling and direct C-H functionalization reactions. One of the six-membered chelate complexes was found to be an efficient pre-catalyst for mediating the coupling reactions between aryl chlorides and alkenes. The palladium(0) complex could also be effectively applied in the direct C-H functionalization reactions of aryl bromides with 1,2-dimethylimidazole.

Original languageEnglish
Pages (from-to)10375-10388
Number of pages14
JournalDalton Transactions
Volume45
Issue number25
DOIs
Publication statusPublished - 2016 Jan 1

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phosphine
Bearings (structural)
Palladium
Interchanges
Alkenes
Bromides
Conformations
Chlorides
Nuclear magnetic resonance
Single crystals
Ligands
X ray diffraction
Catalysts
carbene

All Science Journal Classification (ASJC) codes

  • Inorganic Chemistry

Cite this

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title = "Well-defined palladium(0) complexes bearing N-heterocyclic carbene and phosphine moieties: Efficient catalytic applications in the Mizoroki-Heck reaction and direct C-H functionalization",
abstract = "Two series of well-defined palladium(0) complexes with phosphine-functionalized N-heterocyclic carbene ligands were prepared. These complexes featured six- and seven-membered chelate rings in the two series. Among the seven-membered chelate complexes, those featuring the PCy2 moiety exhibited observable fluxional behavior on the NMR time scale, corresponding to the interchange between two sets of conformations. Most of these novel complexes were successfully structurally characterized by single-crystal X-ray diffraction studies. These two series of palladium(0) complexes were tested for their potential catalytic applications in two mechanistically distinct reactions, namely, Mizoroki-Heck coupling and direct C-H functionalization reactions. One of the six-membered chelate complexes was found to be an efficient pre-catalyst for mediating the coupling reactions between aryl chlorides and alkenes. The palladium(0) complex could also be effectively applied in the direct C-H functionalization reactions of aryl bromides with 1,2-dimethylimidazole.",
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Well-defined palladium(0) complexes bearing N-heterocyclic carbene and phosphine moieties : Efficient catalytic applications in the Mizoroki-Heck reaction and direct C-H functionalization. / Lee, Jhen Yi; Shen, Jiun Shian; Tzeng, Ru Jiun; Lu, I. Chen; Lii, Jenn Huei; Hu, Ching-Han; Lee, Hon Man.

In: Dalton Transactions, Vol. 45, No. 25, 01.01.2016, p. 10375-10388.

Research output: Contribution to journalArticle

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AU - Lee, Jhen Yi

AU - Shen, Jiun Shian

AU - Tzeng, Ru Jiun

AU - Lu, I. Chen

AU - Lii, Jenn Huei

AU - Hu, Ching-Han

AU - Lee, Hon Man

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