Transition Metal Chemistry

, Volume 43, Issue 4, pp 339–346 | Cite as

Tuning the regioselectivity of (benzimidazolylmethyl)amine palladium(II) complexes in the methoxycarbonylation of hexenes and octenes

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Abstract

Reactions of N-(1H-benzoimidazol-2-ylmethyl-2-methoxy)aniline (L1) and N-(1H-benzoimidazol-2-ylmethyl-2-bromo)aniline (L2) with p-TsOH, Pd(AOc)2 and two equivalents of PPh3 or PCy3 produced the corresponding palladium complexes, [Pd(L1)(OTs)(PPh3)] (1), [Pd(L2)(OTs)(PPh3)] (2) and [Pd(L1)(OTs)(PCy3)] (3), respectively, in good yields. The new palladium complexes 13 and the previously reported complexes [Pd(L1)ClMe] (4) and [Pd(L2)ClMe] (5) gave active catalysts in the methoxycarbonylation of terminal and internal olefins to produce branched and linear esters. The effects of complex structure, nature of phosphine derivative, acid promoter and alkene substrate on the catalytic activities and selectivity have been studied and are herein reported.

Notes

Acknowledgements

The Authors would like to thank NRF-DST Center of Excellence in Catalysis (c*change), National Research Foundation (NRF-South Africa) and the University of KwaZulu-Natal for financial support.

Supplementary material

11243_2018_222_MOESM1_ESM.docx (1.3 mb)
Supplementary material 1 (DOCX 1297 kb)

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Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  1. 1.School of Chemistry and Physics, Pietermaritzburg CampusUniversity of KwaZulu-NatalScottsvilleSouth Africa

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