Selective Arylation of 2-Bromo-4-chlorophenyl-2-bromobutanoate via a Pd-Catalyzed Suzuki Cross-Coupling Reaction and Its Electronic and Non-Linear Optical (NLO) Properties via DFT Studies.

Usman Nazeer,Syed Adnan Ali Shah,Muhammad Zubair,Zainul Amiruddin Zakaria,Ali Raza Shah,Muhammad Nadeem Akhtar,Nasir Rasool,Tariq Mahmood,Asim Mansha,Naveen Kosar,Aqsa Mujahid

doi:10.3390/molecules25153521

Abstract

In the present study, 2-bromo-4-chlorophenyl-2-bromobutanoate (3) was synthesized via the reaction of 2-bromo-4-chlorophenol with 2-bromobutanoyl bromide in the presence of pyridine. A variety of 2-bromo-4-chlorophenyl-2-bromobutanoate derivatives (5a–f) were synthesized with moderate to good yields via a Pd-catalyzed Suzuki cross-coupling reaction. To find out the reactivity and electronic properties of the compounds, Frontier molecular orbital analysis, non-linear optical properties, and molecular electrostatic potential studies were performed.

Highlights

IntroductionCarboxylic esters are an important class of organic compounds, having various biological activities such as antifungal [1], antioxidant [2], anti-inflammatory [3], antiproliferative [4], and anti-bacterial [5], and they have been widely used in the biofuel [6], plasticizer [7], food, and cosmetic industries [8].Molecules 2020, 25, 3521; doi:10.3390/molecules25153521 www.mdpi.com/journal/moleculesMolecules 2020, 25, x FOR PEER REVIEWIn natural product chemistry, esters are well known common intermediates because of their accessibility their accessibility for easyand interconversion theirare stability.Esters are generally synthesized by the for easy interconversion their stability.andEsters generally synthesized by the condensation of condensation of carboxylic acids with alcohols.activation of the carboxyl group followed carboxylic acids with alcohols
We suggest that compound 5c shows a better Non-linear Optical (NLO) response and can be used as an active NLO material in the future
Investigation gave us the idea of electrophilicity and nucleophilicity of the synthesized compounds, and it was envisaged that depression of electron density is highly dependent on the substituent present on an aromatic ring

Summary

Introduction

Carboxylic esters are an important class of organic compounds, having various biological activities such as antifungal [1], antioxidant [2], anti-inflammatory [3], antiproliferative [4], and anti-bacterial [5], and they have been widely used in the biofuel [6], plasticizer [7], food, and cosmetic industries [8].Molecules 2020, 25, 3521; doi:10.3390/molecules25153521 www.mdpi.com/journal/moleculesMolecules 2020, 25, x FOR PEER REVIEWIn natural product chemistry, esters are well known common intermediates because of their accessibility their accessibility for easyand interconversion theirare stability.Esters are generally synthesized by the for easy interconversion their stability.andEsters generally synthesized by the condensation of condensation of carboxylic acids with alcohols.activation of the carboxyl group followed carboxylic acids with alcohols. Carboxylic esters are an important class of organic compounds, having various biological activities such as antifungal [1], antioxidant [2], anti-inflammatory [3], antiproliferative [4], and anti-bacterial [5], and they have been widely used in the biofuel [6], plasticizer [7], food, and cosmetic industries [8]. Esters are well known common intermediates because of their accessibility their accessibility for easyand interconversion theirare stability. Esters are generally synthesized by the for easy interconversion their stability.and. Esters generally synthesized by the condensation of condensation of carboxylic acids with alcohols. Activation of the carboxyl group followed carboxylic acids with alcohols. Activation of the carboxyl group followed by reaction by reaction withalcohol suitableisalcohol one most of the most familiar methods ester formation[9]. With suitable one ofis the familiar methods for for ester formation

Methods

Discussion

Conclusion