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N-heterocyclic carbene; Palladium; PEPPSI; Mizoroki-Heck reaction; aqueous media

A new air and moisture stable PEPPSI (PEPPSI: pyridine-enhanced pre-catalyst preparation, stabilisation, and initiation) themed palladium N-heterocyclic carbene (NHC) complex [Pd(L)Br₂(Py)] (1) [L:2-flurobenzyl)-1-(4-methoxyphenyl)-1H-imidazolline-2-ylidene] was synthesized and characterized. The structure of complex 1 was determined by X-ray single-crystal analysis. The palladium center in 1 adopted a square planar geometry with carbene and pyridine ligands occupying the mutual trans position. The complex 1 was employed to catalyze the Mizoroki-Heck cross-coupling reactions of aryl bromides/iodides with styrene in water. To the best of our knowledge, this is the first report where a Pd-PEPPSI catalyst was successfully employed in aqueous-phase Mizoroki-Heck reaction. Good to excellent yields of cross-coupling products were obtained with a range of representative aryl bromides/iodides under relatively mild conditions(100 °C, 1 mol% of 1).

DHRUBAJIT BORAH^{1 2} BISWAJIT SAHA^{3 4} BIPUL SARMA⁵ PANKAJ DAS¹

1. Department of Chemistry, Dibrugarh University, Dibrugarh, Assam 786004, India
2. Department of Chemistry, N. N. Saikia College, Titabar, Assam 785630, India
3. Advanced Materials Group, Materials Sciences and Technology Division, CSIR-North East Institute of Science and Technology, Jorhat, Assam 785006, India
4. Academy of Scientific and Innovative Research (AcSIR), CSIR-NEIST Campus, Jorhat, Assam 785006, India
5. Department of Chemical Sciences, Tezpur University, Napaam, Tezpur, Assam 784028, India

Published

11 March 2020

Manuscript received

29 August 2019

Manuscript revised

7 November 2019

Accepted

10 November 2019