Nicotine functionalized‐silica palladium (II) complex: a highly efficient, environmentally benign and recyclable nanocatalyst for C‐C bond forming reactions under mild conditions

Abstract

An environmentally friendly silica‐grafted nicotine‐based palladium(II) complex was successfully prepared and evaluated for the first time as novel and efficient nanocatalyst in C‐C bond forming reactions. Grafted‐nicotine in this catalytic system plays an important role, and as an effective ligand and a quaternary ammonium salt demonstrates an efficient stabilizing effect on the Pd(II) species by a synergistic effect of coordination and electrostatic interactions. The catalyst was well characterized by FT‐IR, CHN, XRD, TEM, SEM–EDX, ICP and TG analysis, and demonstrated a highly efficient catalytic activity in the reaction system under phosphine‐free and low Pd loading conditions, and the coupled products were produced in good to excellent yields. Furthermore, the catalyst can be easily recovered and reused without a significant loss of activity. Copyright © 2016 John Wiley & Sons, Ltd.

Copper-free Sonogashira cross-coupling reactions: an overview

“…Based on the optimal condition, different aryl bromides reacted with phenylacetylene and afforded the corresponding Sonogashira products ( Scheme 73 ). 132 …”

“…Based on the optimal condition, different aryl bromides reacted with phenylacetylene and afforded the corresponding Sonogashira products (Scheme 73). 132 A nano tetramine palladium(0) complex catalyst was efficiently used as an effective heterogeneous catalyst in the Cu-free Sonogashira coupling reaction in DMF. Analysis of the reaction mixture demonstrated that the leaching of Pd from the catalyst was insignicant.…”

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes†

“…Hajipour and co‐workers illustrated a silica‐grafted nicotine‐based Pd(II) complex 31 for Sonogashira coupling (Figure 5). [ 94 ] The grafted‐nicotine acts not only as an effective ligand, but also a quaternary ammonium salt. It is believed that the grafted‐nicotine gives a stabilizing effect on the Pd(II) species by a synergistic effect of coordination and electrostatic interactions.…”

Functionalized Silica Matrices and Palladium: A Versatile Heterogeneous Catalyst for Suzuki, Heck, and Sonogashira Reactions

“…Silica matrices including functionalized silica gel, silica yolk–shell, nanoporous silica, SBA-15, SBA-16, MCM-41, MCM-48, SiO 2 aerogels, silica wet gel, fluorous silica gel, and organosilicas have been used to support PdNPs on their surfaces. These materials are utilized in Suzuki–Miyaura, Heck, and Sonogashira cross-coupling reactions because they possess excellent reactivities under sustainable conditions and can be readily recovered and reused by simple filtration after completion of the reaction.…”