Pd@GO catalyzed stereo- and regio-selective addition of arenes to alkynes and synthesis of coumarins via C-H functionalization.

A stereo- and regio-selective addition of arenes to alkynes via C-H bond functionalization has been developed using palladium nanoparticles supported on graphite oxide (Pd@GO) as the reusable catalyst. The prepared catalyst was characterized by various spectroscopic techniques such as FT-IR, TEM, SEM, EDX, P-XRD, and XPS analysis. The thermal stability of the catalyst was established by TGA. The C-H functionalized products were obtained in good to excellent yields (69-92%) at room temperature. The methodology further extended to the synthesis of biologically and pharmaceutically important coumarin molecules from phenols and alkynes. Good to excellent yields of the coumarins (74-92%) were obtained. After the reaction, the catalyst was separated by centrifugation followed by filtration. The recovered catalyst was washed and reused up to five cycles. The advantages of this method are the simple procedure of the catalyst preparation, high catalytic efficiency, high selectivity, good functional group tolerance, low catalyst loading, and gram-scale synthesis.

A sustainable avenue for the synthesis of propargylamines and benzofurans using a Cu-functionalized MIL-101(Cr) as a reusable heterogeneous catalyst.

A heterogeneous copper-catalyzed A3 coupling reaction of aldehydes, amines, and alkynes for the synthesis of propargylamines and benzofurans has been developed. Here, the modified metal-organic framework MIL-101(Cr)-SB-Cu complex was chosen as the heterogeneous copper catalyst and prepared via post-synthetic modification of amino-functionalized MIL-101(Cr). The structure, morphology, thermal stability, and copper content of the catalyst were determined by FT-IR, PXRD, SEM, TEM, EDX, TGA, XPS, and ICP-OES. The catalyst shows high catalytic activity for the aforementioned reactions under solvent-free reaction conditions. High yields, low catalyst loading, easy catalyst recovery and reusability with not much shrink in catalytic activity, and a good yield of 82% in gram-scale synthesis are some of the benefits of this protocol that drove it towards sustainability.

Versatile and Sustainable Approach to Access Biologically Relevant Chromeno[2,3-b]pyridine and Benzylpyrazolyl Coumarin Derivatives Using Graphitic Carbon Nitride as a Reusable Heterogeneous Catalyst.

Herein, the synthesis of graphitic carbon nitride (g-C3N4) via the simple heating of cheap and readily available urea as the starting material has been reported. The catalytic activity of the prepared g-C3N4 was investigated for the synthesis of chromeno[2,3-b]pyridine and benzylpyrazolyl coumarin derivatives in an ethanol medium. The reactions were performed under mild conditions to achieve widely functionalized target products in a one-pot operation. The as-synthesized g-C3N4, being a heterogeneous catalyst, demonstrates excellent recyclability up to the 5th consecutive run without a significant decrease in its catalytic activity and yield of the product. A gram-scale reaction was performed to demonstrate the industrial applications of the present protocol. The green chemistry metrics such as environmental factor (E-factor), atom economy (AE), carbon efficiency (CE), and reaction mass efficiency (RME) were calculated and found to be very close to the ideal values. Additionally, operation simplicity, wide substrate scope, easy reusability of the catalyst, and avoidance of metal contamination in the products drive the process toward green and sustainable development.

Copper Oxide/Reduced Graphene Oxide Nanocomposite-Catalyzed Synthesis of Flavanones and Flavanones with Triazole Hybrid Molecules in One Pot: A Green and Sustainable Approach.

An efficient, green, and sustainable synthesis of new hybrid molecules containing flavanone with triazole by merging the Michael addition and Click reaction using a copper oxide/reduced graphene oxide nanocomposite in one pot is reported. The catalyst can easily be recycled and reused in seven consecutive runs without compromising the product yields. Other notable advantages include using water as a reaction medium and obtaining good to excellent yields, low catalyst loading, high atom efficiency, high substrate variation, and good results in the gram scale reaction.

A coumarin based Schiff base probe for selective fluorescence detection of Al3+ and its application in live cell imaging.

A new coumarin based Schiff base compound, CSB-1 has been synthesized to detect metal ion based on the chelation enhanced fluorescence (CHEF). The cation binding properties of CSB-1 was thoroughly examined in UV-vis and fluorescence spectroscopy. In fluorescence spectroscopy the compound showed high selectivity toward Al3+ ion and the Al3+ can be quantified in mixed aqueous buffer solution (MeOH: 0.01M HEPES Buffer; 9:1; v/v) at pH7.4 as well as in BSA media. The fluorescence intensity of CSB-1 was enhanced by ~24 fold after addition of only five equivalents of Al3+. The fluorescence titration of CSB-1 with Al3+ in mixed aqueous buffer afforded a binding constant, Ka=(1.06±0.2)×104M-1. The colour change from light yellow to colourless and the appearance of blue fluorescence, which can be observed by the naked eye, provides a real-time method for Al3+ sensing. Further the live cell imaging study indicated that the detection of intracellular Al3+ ions are also readily possible in living cell.