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Palladium Catalyzed Annulation of Morita‐Baylis‐Hillman Adducts: Synthesis of Indene and Indanone Derivatives
Author(s) -
Rajan Sruthi Pambingal,
Venu Saranya Thachora,
Anas Saithalavi
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201903515
Subject(s) - indene , chemistry , adduct , annulation , catalysis , medicinal chemistry , palladium , organic chemistry
Abstract Concise and efficient methods for the syntheses of functionalized Indene and Indanone derivatives from Morita‐Baylis Hillman (MBH) alcohols via Palladium catalyzed annulations are described. The formation and nature of the product was based on the MBH adduct used and the reaction conditions established after detailed optimization studies. The reaction of Baylis‐Hillman alcohols ( 1   a – m ) in presence of Pd(OAc) 2 (5 mol %), P(o‐Tol) 3 (20 mol %) , AgOAc (1 eq.) and Na 2 CO 3 (2 eq.) in Dioxane at 120 °C under Nitrogen atmosphere provided substituted indenes ( 2   a – m ) in good to excellent yields. While, Indanone derivatives ( 4   a – f ) are obtained from o ‐halo substituted MBH adducts ( 3   a – l ) when subjected to reaction with Pd(OAc) 2 (3 mol %) and K 3 PO 4 (2.5 eq.) in DMA at 140 °C in the absence of any ligand or additive.

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