Suzuki−Miyaura Reactions of (4-bromophenyl)-4,6-dichloropyrimidine through Commercially Available Palladium Catalyst: Synthesis, Optimization and Their Structural Aspects Identification through Computational Studies

Ayesha Malik; Nasir Rasool; Iram Kanwal; Muhammad Ali Hashmi; Ameer Fawad Zahoor; Gulraiz Ahmad; Ataf Ali Altaf; Syed Adnan Ali Shah; Sadia Sultan; Zainul Amiruddin Zakaria

LAPSE

Living Archive for Process Systems Engineering

LAPSE:2021.0341

Published Article

LAPSE:2021.0341

Suzuki−Miyaura Reactions of (4-bromophenyl)-4,6-dichloropyrimidine through Commercially Available Palladium Catalyst: Synthesis, Optimization and Their Structural Aspects Identification through Computational Studies

Ayesha Malik, Nasir Rasool, Iram Kanwal, Muhammad Ali Hashmi, Ameer Fawad Zahoor, Gulraiz Ahmad, Ataf Ali Altaf, Syed Adnan Ali Shah, Sadia Sultan, Zainul Amiruddin Zakaria

May 4, 2021

5-(4-bromophenyl)-4,6-dichloropyrimidine was arylated with several aryl/heteroaryl boronic acids via the Suzuki cross-coupling reaction by using Pd(0) catalyst to yield novel pyrimidine analogs (3a-h). It was optimized so that good yields were obtained when 5 mol % Pd(PPh3)4 was used along with K3PO4 and 1,4-Dioxane. Electron-rich boronic acids were succeeded to produce good yields of products. Density functional theory (DFT) calculations were also applied on these new compounds to analyze their reactivity descriptors and electronic and structural relationship. According to DFT studies, compound 3f is the most reactive one, while 3g is the most stable one. As per DFT studies, the hyperpolarizability (β) values of these compounds do not show them as very good non-linear optical (NLO) materials. Compound 3f has the highest β value among all the compounds under study but still it is not high enough to render it a potent NLO material.

Record ID

LAPSE:2021.0341

Keywords

DFT, FMO, Pd catalyst, reactivity descriptors, Suzuki–Miyaura

Subject

Reaction Engineering

Suggested Citation

Malik A, Rasool N, Kanwal I, Hashmi MA, Zahoor AF, Ahmad G, Altaf AA, Shah SAA, Sultan S, Zakaria ZA. Suzuki−Miyaura Reactions of (4-bromophenyl)-4,6-dichloropyrimidine through Commercially Available Palladium Catalyst: Synthesis, Optimization and Their Structural Aspects Identification through Computational Studies. (2021). LAPSE:2021.0341

Author Affiliations

Malik A: Department of Chemistry, Government College University, Faisalabad 38000, Pakistan
Rasool N: Department of Chemistry, Government College University, Faisalabad 38000, Pakistan
Kanwal I: Department of Chemistry, Government College University, Faisalabad 38000, Pakistan
Hashmi MA: Department of Chemistry, University of Education, Attock Campus, Attock 43600, Pakistan [ORCID]
Zahoor AF: Department of Chemistry, Government College University, Faisalabad 38000, Pakistan
Ahmad G: Department of Chemistry, Government College University, Faisalabad 38000, Pakistan
Altaf AA: Centre of Catalysis and Energy Research, Department of Chemistry, University of Okara, Okara 56300, Pakistan; Department of Chemistry, University of Okara, Okara 56300, Pakistan [ORCID]
Shah SAA: Faculty of Pharmacy, Universiti Teknologi MARA Cawangan Selangor Kampus Puncak Alam, Bandar Puncak Alam, Selangor 42300, Malaysia; Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Universiti Teknologi MARA Cawangan Selangor Kampus Puncak [ORCID]
Sultan S: Faculty of Pharmacy, Universiti Teknologi MARA Cawangan Selangor Kampus Puncak Alam, Bandar Puncak Alam, Selangor 42300, Malaysia; Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Universiti Teknologi MARA Cawangan Selangor Kampus Puncak
Zakaria ZA: Department of Biomedical Science, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, UPM Serdang, Selangor 43400, Malaysia; Integrative Pharmacogenomics Institute (iPromise), Universiti Teknologi MARA Cawangan Selangor Kampus Puncak Alam, [ORCID]

Journal Name

Processes

Volume

8

Issue

11

Article Number

E1342

Year

2020

Publication Date

2020-10-23