A Comparative Study of Dibenzylideneacetone Palladium Complexes in Catalysis

Weber, Philip; Biafora, Agostino; Doppiu, Angelino; Bongard, Hans-Josef; Kelm, Harald; Gooßen, Lukas J.

doi:10.1021/acs.oprd.9b00214

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A Comparative Study of Dibenzylideneacetone Palladium Complexes in Catalysis

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Bongard, Hans-Josef
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Weber, P., Biafora, A., Doppiu, A., Bongard, H.-J., Kelm, H., & Gooßen, L. J. (2019). A Comparative Study of Dibenzylideneacetone Palladium Complexes in Catalysis. Organic Process Research & Development, 23(7), 1462-1470. doi:10.1021/acs.oprd.9b00214.

Cite as: https://hdl.handle.net/21.11116/0000-0004-8E6E-2

Abstract

Commercial Pd_x(dba)_y from various suppliers was found to vary considerably in appearance, homogeneity, purity, and catalytic activity. The Buchwald–Hartwig amination of 4-bromoanisole (5) with aniline (6) was established as a sensitive test reaction to probe the efficiency of Pd_x(dba)_y batches in catalytic transformations. The yields obtained with 17 different Pd_x(dba)_y batches ranged from 10% to nearly quantitative and could not be predicted reliably on the basis of any physical or spectroscopic descriptor alone. The best results in the catalytic test reaction were consistently achieved with a self-made slowly crystallized Pd₂(dba)₃·toluene adduct. A protocol is disclosed that allows batches of Pd_x(dba)_y with unsatisfactory or inconsistent performance to be converted into this reliable precatalyst.