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  • Title: Synthesis and structure of Pd(II) pincer complexes: catalytic application in β-alkylation of secondary alcohols involving sequential dehydrogenation of alcohols via the borrowing hydrogen approach.
    Author: Pranesh Kavin S, Ramesh R.
    Journal: Dalton Trans; 2023 Jul 25; 52(29):10038-10044. PubMed ID: 37409425.
    Abstract:
    Herein, we report an efficient and sustainable approach for the selective synthesis of ketones by palladium pincer catalyzed β-alkylation of secondary alcohols with aromatic primary alcohols via the borrowing hydrogen (BH) approach for the first time. A set of new Pd(II) ONO pincer complexes was synthesized and characterised by elemental analysis and spectral techniques (FT-IR, NMR and HRMS). The solid-state molecular structure of one the complexes was corroborated by X-ray crystallography. A range of α-alkylated ketone derivatives (25 examples) was obtained in excellent yields up to 95% through sequential dehydrogenative coupling of secondary and primary alcohols with 0.5 mol% catalyst loading with a substoichiometric amount of the base. Control experiment studies were carried out for the coupling reactions which revealed that the reaction involves an aldehyde, a ketone and chalcone intermediates, and eventually established the borrowing hydrogen strategy. Gratifyingly, this protocol is simple and atom economical, with water/hydrogen as byproducts. In addition, large-scale synthesis also demonstrated the synthetic usefulness of the present protocol.
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