Palladium anchored on amine-functionalized K10 as an efficient, heterogeneous and reusable catalyst for carbonylative Sonogashira reaction

• Published in: Applied catalysis. A, General General, 2015-10, Vol.506, p.237-245
• Main Authors: Chavan, Sujit P., Varadwaj, G.Bishwa Bidita, Parida, Kulamani, Bhanage, Bhalchandra M.
• Format: Article
• Language: English
• Subjects: Alkynyl ketones; Carbonylative Sonogashira reaction; Dibenzoylmethane; Heterogeneous catalysis; Pd(II)APTES@K10
• ISSN: 0926-860X; 1873-3875
• DOI: 10.1016/j.apcata.2015.09.019

[Display omitted] •Immobilization of palladium (II) chloride on the amine functionalized K10.•The wide variety of alkynyl ketones were synthesized in good to excellent yields.•Recovery of catalyst by simple filtration and its reuse up to four consecutive cycles. The present work describes the immobilization of palladium chloride (II) on the amine functionalized K10 support and its application toward the carbonylative Sonogashira reactions. The various catalyst characterization techniques revealed the successful grafting of APTES moiety on the K10 clay surface through covalent bonding and Pd with the NH2 groups of APTES@K10 through co-ordinate bonding. The immobilized catalyst was successively applied for copper and phosphine free carbonylative Sonogashira reaction of aryl and hetero aryl iodides with terminal alkynes. To our delight, the electron withdrawing aryl halides can be efficiently utilized as an electrophiles giving higher selectivity toward carbonylated products. Moreover, dibenzoylmethane which is a potential synthetic intermediate in organic transformation has been also synthesized using this protocol. Recovery of catalyst by simple filtration and its reuse up to four consecutive cycles ensure the robustness of present catalytic protocol.