Suzuki-Miyaura cross-coupling of aryl chlorides catalyzed by palladium precatalysts of N/O-functionalized pyrazolyl ligands

Alex John, Mobin M. Shaikh, Prasenjit Ghosh

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15 Scopus citations

Abstract

A series of palladium complexes, trans-[1-(R)-pz3,5-Me2]2PdCl2 {R = CH2CONH(2,6-i-Pr2-C6H3) (1b) and 2-(OH)-C6H10 (2b)}, supported over N/O-functionalized pyrazole derived ligands effectively catalyzed the more challenging Suzuki-Miyaura cross-coupling of a variety of activated aryl chlorides with phenyl boronic acid in air in a mixed-aqueous medium (DMF:H2O, v/v = 9:1) in moderate to excellent yields. Besides the commonly encountered C sp2-Csp2 coupling, the 1b and 2b precatalysts also catalyzed the relatively difficult Csp2-Csp3 coupling of benzyl chloride with phenyl boronic acid. The 1b and 2b complexes were synthesized by the direct reaction of the respective N/O-functionalized pyrazolyl ligands, 1a and 2a, with (COD)PdCl2 in 62-66% yields. The stability of the pyrazole-palladium interaction in the 1b and 2b complexes has been attributed to the deeply buried Npyrazole-Pd interaction as evidenced from the density functional theory (DFT) studies.

Original languageEnglish (US)
Pages (from-to)3113-3121
Number of pages9
JournalInorganica Chimica Acta
Volume363
Issue number12
DOIs
StatePublished - Oct 15 2010

Bibliographical note

Funding Information:
We thank DST, New Delhi, for financial support of this research. We are grateful to the National Single Crystal X-ray Diffraction Facility and Sophisticated Analytical Instrument Facility at IIT Bombay, India, for the crystallographic and other characterization data. Computational facilities from the IIT Bombay Computer Center are gratefully acknowledged. A.J. thanks CSIR, New Delhi for research fellowship.

Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.

Keywords

  • Aryl chlorides
  • Catalysis
  • Density functional theory
  • N/O-functionalized
  • Pyrazole
  • Suzuki-Miyaura

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