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PtO₂/PTSA system catalyzed regioselective hydration of internal arylalkynes bearing electron withdrawing groups.

ABSTRACT: A highly efficient PtO₂/PTSA catalyst system for the hydration of a wide array of alkynes was developed. This method proved to be compatible with a large range of functional groups and the ketone products were obtained in high yields. The scope of this methodology was also extended to the synthesis of 3-aryl-isochromenones, -indoles and -benzofurans.

SUBMITTER: Lin HP

PROVIDER: S-EPMC9079276 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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PtO<sub>2</sub>/PTSA system catalyzed regioselective hydration of internal arylalkynes bearing electron withdrawing groups.

Lin Hsin-Ping HP Ibrahim Nada N Provot Olivier O Alami Mouad M Hamze Abdallah A

RSC advances 20180323 21

A highly efficient PtO<sub>2</sub>/PTSA catalyst system for the hydration of a wide array of alkynes was developed. This method proved to be compatible with a large range of functional groups and the ketone products were obtained in high yields. The scope of this methodology was also extended to the synthesis of 3-aryl-isochromenones, -indoles and -benzofurans. ...[more]

PMID: 35542815

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Project description:The structure-property relationship study of a series of cationic Ir(III) complexes in the form of [Ir(C^N)2(dtBubpy)]PF6 [where dtBubpy = 4,4'-di-tert-butyl-2,2'-bipyridine and C^N = cyclometallating ligand bearing an electron-withdrawing group (EWG) at C4 of the phenyl substituent, i.e., -CF3 (1), -OCF3 (2), -SCF3 (3), -SO2CF3 (4)] has been investigated. The physical and optoelectronic properties of the four complexes were comprehensively characterized, including by X-ray diffraction analysis. All the complexes exhibit quasireversible dtBubpy-based reductions from -1.29 to -1.34 V (vs SCE). The oxidation processes are likewise quasireversible (metal + C^N ligand) and are between 1.54 and 1.72 V (vs SCE). The relative oxidation potentials follow a general trend associated with the Hammett parameter (σ) of the EWGs. Surprisingly, complex 4 bearing the strongest EWG does not adhere to the expected Hammett behavior and was found to exhibit red-shifted absorption and emission maxima. Nevertheless, the concept of introducing EWGs was found to be generally useful in blue-shifting the emission maxima of the complexes (λem = 484-545 nm) compared to that of the prototype complex [Ir(ppy)2(dtBubpy)]PF6 (where ppy = 2-phenylpyridinato) (λem = 591 nm). The complexes were found to be bright emitters in solution at room temperature (ΦPL = 45-66%) with microsecond excited-state lifetimes (τe = 1.14-4.28 μs). The photophysical properties along with density functional theory (DFT) calculations suggest that the emission of these complexes originates from mixed contributions from ligand-centered (LC) transitions and mixed metal-to-ligand and ligand-to-ligand charge transfer (LLCT/MLCT) transitions, depending on the EWG. In complexes 1, 3, and 4 the 3LC character is prominent over the mixed 3CT character, while in complex 2, the mixed 3CT character is much more pronounced, as demonstrated by DFT calculations and the observed positive solvatochromism effect. Due to the quasireversible nature of the oxidation and reduction waves, fabrication of light-emitting electrochemical cells (LEECs) using these complexes as emitters was possible with the LEECs showing moderate efficiencies.

Dataset Information

PtO₂/PTSA system catalyzed regioselective hydration of internal arylalkynes bearing electron withdrawing groups.

Publications

PtO<sub>2</sub>/PTSA system catalyzed regioselective hydration of internal arylalkynes bearing electron withdrawing groups.

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Dataset Information

PtO2/PTSA system catalyzed regioselective hydration of internal arylalkynes bearing electron withdrawing groups.

Publications

PtO<sub>2</sub>/PTSA system catalyzed regioselective hydration of internal arylalkynes bearing electron withdrawing groups.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets

PtO₂/PTSA system catalyzed regioselective hydration of internal arylalkynes bearing electron withdrawing groups.