Binaphthyl stabilized palladium nanoparticles (Pd-BNP) catalyzed synthesis of biologically active phenanthridinones via domino C–H activation followed by C–C and C–N bond formation strategy in open air conditions is disclosed. This method works well with a broad range of N-methoxybenzamides and aryliodides substrates with different functional groups. The reaction is catalyzed by 1.5 mol% of heterogeneous Pd-BNP catalyst and afforded the phenanthridinones up to 87% yield with exclusive regioselectivity. Hot centrifuge test, UV spectroscopy analysis and Hg poisoning test are proved the heterogeneous nature of Pd-BNP catalyst. © 2018 Elsevier Inc.

Govindasamy Sekar

Department Of Chemistry

Rajib Saha

Catalyst poisoning

Chemical activation

Nanocatalysts

Nanoparticles

Reaction kinetics

Synthesis (chemical)

Ultraviolet spectroscopy

directing groups

Domino reactions

Palladium nanoparticles

PHENANTHRIDINONES

REUSABLE CATALYSTS

Palladium compounds

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Journal of Catalysis

An efficient methodology for the selective and controlled oxidation of petroleum waste methylarenes/alkylarenes to aromatic carboxylic acids/ketone using easily recoverable and recyclable binaphthyl stabilized Pt nanoparticles (Pt-BNP) as a catalyst has been developed. The greener oxidant aq. tert-butyl hydroperoxide (TBHP) and green solvent water have been utilized in this oxidation reaction. The methodology is well tolerated with different functional groups. The less reactive electron deficient toluenes are also oxidized by Pt-BNP and gave a good yield of corresponding carboxylic acids with a high turnover number (TON) 738-1448. The Pt-BNP catalyst was recovered and reused up to five catalytic cycles. The heterogeneous test suggested that the reaction is catalyzed by heterogeneous Pt-BNP catalysts. Based on control experiments and literature reports, a possible reaction mechanism has been proposed. © 2019 Elsevier B.V.

Applied Catalysis B: Environmental

Selective oxidation of alkylarenes to aromatic acids/ketone in water by using reusable binaphthyl stabilized Pt nanoparticles (Pt-BNP) as catalyst

Transition-metal nanoparticles (NPs) gained interest as a catalyst due to their high reactivity and recyclability. Monometallic NPs are less catalytic active compared to homogeneous counterparts as less number of catalytic active metal atoms are present on the surface of NPs and metal atoms present in the core part of the NPs are not utilized. It is necessary to synthesize a stable, reusable, highly reactive and economic catalyst which contain a more number of catalytic active precious metal atoms on the surface of NPs. Here in we have synthesized metal-carbon bond stabilized, alloy structured Pd/Cu bimetallic nanoparticles using binaphthyl moiety as a stabilizer (Pd/Cu-BNP). The enrichment of catalytically active precious Pd atoms over inexpensive Cu on the surface was observed with a narrow size distribution of the nanoparticles (average diameter 3 ± 0.5 nm). The Pd/Cu-BNP was used as an efficient and recyclable catalyst for the synthesis of polycyclic triazoles through domino alkyne insertion and C[sbnd]H bond functionalization reaction sequence. © 2019

Surface enriched palladium on palladium-copper bimetallic nanoparticles as catalyst for polycyclic triazoles synthesis

A novel method to synthesize isoquinolones via oxidative annulation of N-alkoxy benzamides and alkynes using binaphthyl-stabilized palladium nanoparticles (Pd-BNP) as catalyst has been developed. This methodology affords various isoquinolone derivatives in good to excellent yields with high regioselectivities in the presence of air as oxidant. N-Methoxybenzothioamide was also found to undergo oxidative annulation with alkyne successfully and provided a sulfur analogue of isoquinolones in moderate yields. The Pd-BNP catalyst was easily recovered and reused up to four times without any apparent agglomeration. (Figure presented.). © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Advanced Synthesis and Catalysis

Palladium-Nanoparticles-Catalyzed Oxidative Annulation of Benzamides with Alkynes for the Synthesis of Isoquinolones

An efficient, binaphthyl-backbone-stabilized palladium nanoparticles (Pd-BNP) catalyst for the 1,4-addition of aryl halides to enones has been developed. The scope of the reaction has been studied with various substituted and sterically hindered aryl halides and enones to afford the conjugate addition products in good to excellent yields. The catalyst has been recovered and reused up to five times without any appreciable change in particle size or reactivity. (Figure presented.). © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Stable and Reusable Palladium Nanoparticles-Catalyzed Conjugate Addition of Aryl Iodides to Enones: Route to Reductive Heck Products

Chiral nanoparticles have become one of the most versatile catalyst for the effective construction of chiral organic moieties. Recently, bimetallic nanoparticles as catalysts have gained interest among the chemists. The presence of hetero metal–metal interactions has modified the surface of the catalyst both electronically and geometrically to show unique activities, selectivities and possess an improved stability than the corresponding monometallic catalyst. In this review, the newly emerging bimetallic chiral nanoparticle catalysts (Rh/Co, Cu/Fe, Pd/Fe, Pt/Fe, Pd/Au, Rh/Ag, etc.) and their application in asymmetric Pauson–Khand reactions, hydrosilylation, Suzuki–Miyaura coupling, α-arylation of tetralones, reduction of ketones, allylation of nitrobenzaldehyde, 1,4-additon reactions and arylation of aldimines have been discussed. © 2016 Elsevier Ltd

Tetrahedron Letters

Bimetallic chiral nanoparticles as catalysts for asymmetric synthesis

A binaphthyl-supported Pd nanoparticles (Pd-BNP)-catalyzed aminocarbonylation of aryl iodides in the presence of carbon monoxide and amines for the synthesis of amides has been developed. This methodology provides an efficient route for the synthesis of a COX-2 enzyme inhibitor having anti-inflammatory activity. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Stable and Reusable Binaphthyl-Supported Palladium Catalyst for Aminocarbonylation of Aryl Iodides

A phosphine-free stable palladium nanocatalyst was used for an efficient synthesis of polysubstituted olefins from N-tosylhydrazones and aryl iodides. This methodology was successfully utilized in the synthesis of biologically important tamoxifen and isocombretastatin A4. The nanocatalyst was easily recovered and reused without any apparent loss in size and catalytic activity. © 2014 American Chemical Society.

Journal	Journal of Catalysis
Publisher	Academic Press Inc.
ISSN	00219517
Open Access	No