Palladium Nanoparticles‐Catalyzed Synthesis of Indanone Derivatives via Intramolecular Reductive Heck Reaction

Abstract

An efficient protocol for the straightforward, single-step synthesis of 3-aryl-1-indanones from 2'iodochalcone via reductive Heck reaction using phosphine free, stable and reusable binaphthyl stabilized palladium nanoparticle (Pd-BNP) as a catalyst has been described. An immense array of substrate scope with electron-rich and deficient 2'-iodochalcones have been synthesized. Further derivatization of product indanones have been achieved successfully. The heterogeneous nature of the Pd-BNP has been validated by centrifugation test and mercury poisoning experiment. Pd-BNP has been successfully recycled up to 5 cycles without any significant loss in reaction yield and particle size of nanoparticles, confirmed by TEM analysis. 3-(4-(Trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-one(2 r): 78% yield (53.8 mg); Yellow liquid; R f 0.53 (10% ethyl acetate in hexanes); 1 H NMR (400 MHz, CDCl 3 ): δ 2.66 (dd, cm À 1 ; HRMS (m/z): [M + Na] + calcd for C 16 H 11 OF 3 Na: 299.0660; found: 299.0651. 3-(3-Nitrophenyl)-2,3-dihydro-1H-inden-1-one (2 s): 70% yield (44.3 mg); Greenish solid; mp 125°C; R f 0.42 (20% ethyl acetate in hexanes); 1 H NMR (400 MHz, CDCl 3 ): δ 2.66 (dd,

Palladium-Nanoparticles Biohybrids in Applied Chemistry

“…These results demonstrate the potential applicability of these biohybrids in this C-C bonding reaction, for example, in the production of more complex molecules, key intermediates in the drug synthesis was similar for other Pd nanocatalysts, as previously described in [27][28][29].…”

Efficient kinetic resolution in the asymmetric transfer hydrogenation of 3-aryl-indanones: applications to a short synthesis of (+)-indatraline and a formal synthesis of (R)-tolterodine

“…The requisite racemic 3-arylindanones used for this purpose were prepared by triic acidcatalyzed condensation reactions between the requisite of cinnamic acids and arenes (Scheme 3, Method A), [43][44][45] or Pdcatalyzed intramolecular reductive Heck cyclization of the corresponding 2 0 -bromochalcones (Method B). 46,47 The results show that 3-arylindanones 1, containing an assortment of electron-donating and -withdrawing substituents, undergo ATH-KR reactions under the optimized conditions within 10 h to generate in most cases the corresponding cis-3-aryl-1-indanols (R,R)-2 and unreacted 3-aryl-1-indanones (S)-1 with excellent stereoselectivities (Table 2).…”

A novel thermoregulated phase-transfer catalysis system for chiral nano-Pt-catalyzed asymmetric hydrogenation

“…Moreover, with the purpose of obtaining further information on the nature of the chiral nano-Pt catalyst, mercury poisoning experiments were conducted, which are widely used to determine whether the catalyst was heterogeneous or not. 35,36 The experimental results are shown in Table 4. When Hg (Hg/Pt = 1000, molar ratio) was added before the start of the reaction, the conversion of MBF was only 4% (Table 4, entry 2).…”