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

doi:10.1039/C6DT01323F

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,^a Jiun-Shian Shen,^a Ru-Jiun Tzeng,^a I-Chen Lu,^a Jenn-Huei Lii,^a Ching-Han Hu^a and Hon Man Lee*^a

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* Corresponding authors

^a Department of Chemistry, National Changhua University of Education, Changhua 50058, Republic of China
E-mail: leehm@cc.ncue.edu.tw
Fax: +8864 7211190
Tel: +886 4 7232105 ext. 3523

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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Publication details

The article was received on 06 Apr 2016, accepted on 23 May 2016 and first published on 23 May 2016

Article type: Paper

DOI: 10.1039/C6DT01323F

Citation: Dalton Trans., 2016,45, 10375-10388

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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

J. Lee, J. Shen, R. Tzeng, I. Lu, J. Lii, C. Hu and H. M. Lee, Dalton Trans., 2016, 45, 10375
DOI: 10.1039/C6DT01323F
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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

Abstract

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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

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