Selenated NHC-Pd(II) catalyzed Suzuki-Miyaura coupling of ferrocene substituted β-chloro-cinnamaldehydes, acrylonitriles and malononitriles for the synthesis of novel ferrocene derivatives and their solvatochromic studies

Suzuki-Miyaura coupling reaction between ferrocenyl/phenyl derivatives of (2-formyl-1-chlorovinyl) ferrocene, 3-chloro-3-ferrocenylacrylonitrile and (3-chloro-3-ferrocenylallylidene)malononitrile and aryl-boronic acid in the catalytic presence of a selenated NHC-Pd(II) full pincer complex was accomplished. Significantly, the couplings take place in water under normal atmospheric conditions, in contrast to many earlier reported Pd-catalysed reactions requiring inert atmosphere conditions. Solvatochromic studies of new ferrocene compounds revealed some interesting changes. Aggregation studies showed an increase of the absorbance with decrease of water content in the water/DMSO solvent mixture. (c) 2021 Elsevier B.V. All rights reserved.

Automated summary

The Suzuki-Miyaura coupling reactions of ferrocenyl/phenyl derivatives with aryl-boronic acid were successfully achieved using a selenated NHC-Pd(II) full pincer complex catalyst in water under normal atmospheric conditions. Solvatochromic studies of new ferrocene compounds revealed interesting changes, while aggregation studies showed an increase in absorbance with decreased water content in the water/DMSO solvent mixture.