Pd(l‐proline)₂complex: an efficient catalyst for Suzuki–Miyaura coupling reaction in neat water

Abstract

An efficient catalytic system for Suzuki–Miyaura coupling reactions in neat water has been developed by using a water‐soluble Pd(l‐proline)2 catalyst. Under the optimized conditions, various biaryl compounds were obtained in good to excellent yields and a wide range of functional groups on the tested substrates were well tolerated. The catalytic system could be reused at least six times with no significant loss in its activity. Copyright © 2014 John Wiley & Sons, Ltd.

Amidophosphine‐stabilized palladium complexes catalyse Suzuki–Miyaura cross‐couplings in aqueous media

“…The palladium‐catalysed Suzuki–Miyaura cross‐coupling reaction between organoboron compounds and organic halides is a very powerful tool for forming carbon–carbon bonds and this makes the Suzuki–Miyaura reaction very important not only in academic research but also in industrial synthesis of fine chemicals and highly complex pharmaceuticals as well as in the synthesis of functionalized π‐conjugated systems . The wide application of the reaction results from the broad functional group tolerance, the commercial availability and low toxicity of the organoborons, and the mild reaction conditions applied .…”

C-S Cross-Coupling Reaction Using a Recyclable Palladium Prolinate Catalyst under Mild and Green Conditions

“…Initially, the synthesis of the catalyst Pd( L ‐Pro) 2 was carried out synthesis following the reports published by Ding et al . Later the protocol for C−S cross‐coupling using Pd( L ‐Pro) 2 was studied in order to optimize the catalytic conditions.…”

“…It can be confirmed by FTIR (See SI), in the reaction involving thiophenol and iodobenzene catalyzed by Pd( L‐ Pro) 2 (post‐reaction‐ catalyst). The FTIR data analysis shows Pd−O stretching band at 542 cm −1 which was present in the Pd( L‐ Pro) 2 . Subsequently, the mechanism pathway after the disulfide elimination, indicates the Pd 0 specie (indicated in an intermediate #3), which is a suitable species to be attacked by the aryl halide via oxidative addition affording #4.…”

Palladium‐catalysed room‐temperature Suzuki–Miyaura coupling in water extract of pomegranate ash, a bio‐derived sustainable and renewable medium

“…However, in these cases the formation of low yields of products or protodebromination is frequently encountered . The selectivity of halogen was found in the presence of free‐amino function (which may otherwise result in a Chan–Lam coupling product or inactivation of the catalyst) (Table , entries 24 and 39). A very high degree of chemoselectivity was observed when the substrates contained mixed halogens (chlorine–bromine ( 1n ), chlorine–iodine ( 1q ) and bromine–iodine ( 1t and 1y )) and identical bromines ( 1r , 1s and 1v ).…”