Palladium [ t‑Bu(PCP)PdOH] Pincer Complex as a Catalyst in the Michael Reaction
Matic Urlep, Matic Lozinšek, Janez Cerkovnik
TL;DR
A palladium pincer complex is shown to efficiently catalyze the Michael reaction, forming carbon–carbon bonds under mild conditions with high yields.
Contribution
The isolation and structural characterization of a reactive palladium intermediate in the Michael reaction is novel.
Findings
The [t-Bu(PCP)Pd(acac)] complex was isolated and characterized by X-ray diffraction.
The catalyst provides Michael adducts in high yields (87–98%) under mild conditions.
The reaction requires low catalyst loading, short times, and minimal solvent.
Abstract
The Michael reaction is a versatile carbon–carbon bond-forming strategy that is efficiently catalyzed by transition metal complexes. We report that the palladium [ t‑Bu(PCP)PdOH] pincer complex effectively activates substrates and forms stable complexes with ketones. The reactive intermediate [ t‑Bu(PCP)Pd(acac)] complex, which is formed in situ from acetylacetone and the [ t‑Bu(PCP)PdOH] complex, was successfully isolated and structurally characterized by single-crystal X-ray diffraction. This complex serves as an active catalyst in the reaction between acetylacetone and various trans-nitrostyrenes, providing the corresponding Michael adducts in high isolated yields (87–98%). The reaction proceeds under mild conditions with a low catalyst loading, short reaction times, and often minimal or no solvent. These results show that PCP-palladium pincer complexes can serve as efficient,…
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Taxonomy
TopicsCatalytic Cross-Coupling Reactions · Catalytic C–H Functionalization Methods · N-Heterocyclic Carbenes in Organic and Inorganic Chemistry