Volume 35, Issue 12 e6439
RESEARCH ARTICLE

Sterically hindered (pyridyl)benzamidine palladium(II) complexes: Syntheses, structural studies, and applications as catalysts in the methoxycarbonylation of olefins

Saphan O. Akiri

Saphan O. Akiri

School of Chemistry and Physics, University of KwaZulu-Natal, Pietermaritzburg, South Africa

Contribution: Conceptualization (equal), Data curation (lead), Formal analysis (lead), ​Investigation (lead), Methodology (lead)

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Stephen O. Ojwach

Corresponding Author

Stephen O. Ojwach

School of Chemistry and Physics, University of KwaZulu-Natal, Pietermaritzburg, South Africa

Correspondence

Stephen O. Ojwach, School of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X01, Scottsville, Pietermaritzburg 3209, South Africa.

Email: [email protected]

Contribution: Conceptualization (equal), Funding acquisition (lead), Project administration (lead), Resources (lead), Supervision (lead)

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First published: 07 September 2021
Citations: 1

Funding information: University of KwaZulu-Natal; DST-NRF (South Africa) Centre of Excellence in Catalysis

Abstract

Reactions of ligands (E)-N′-(2,6-diisopropylphenyl)-N-(4-methylpyridin-2-yl)benzimidamide (L1), (E)-N′-(2,6-diisopropylphenyl)-N-(6-methylpyridin-2-yl)benzimidamide (L2), (E)-N′-(2,6-dimethylphenyl)-N-(6-methylpyridin-2-yl)benzimidamide (L3), (E)-N′-(2,6-dimethylphenyl)-N-(4-methylpyridin-2-yl)benzimidamide (L4), and (E)-N-(6-methylpyridin-2-yl)-N′-phenylbenzimidamide (L5) with [Pd(NCMe)2Cl2] furnished the corresponding palladium(II) precatalysts (Pd1–Pd5), in good yields. Molecular structures of Pd2 and Pd3 revealed that the ligands coordinate in a N^N bidentate mode to afford square planar compounds. Activation of the palladium(II) complexes with para-tolyl sulfonic acid (PTSA) afforded active catalysts in the methoxycarbonylation of a number of alkene. The resultant catalytic activities were controlled by the both the complex structure and alkene substrate. While aliphatic substrates favored the formation of linear esters (>70%), styrene substrate resulted in the formation of predominantly branched esters of up to 91%.

CONFLICT OF INTEREST

The authors declare no known conflicts of interests.

DATA AVAILABILITY STATEMENT

The data that supports the findings of this study are available in the supplementary material of this article.

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