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Synthesis of arylpalladium(II) boronates: confirming the structure and chemical competence of pre-transmetalation intermediates in the Suzuki-Miyaura reaction

Olding, A, Ho, CC ORCID: 0000-0002-7555-0635, Canty, AJ, Lucas, NT, Horne, J ORCID: 0000-0002-1935-2378 and Bissember, AC ORCID: 0000-0001-5515-2878 2021 , 'Synthesis of arylpalladium(II) boronates: confirming the structure and chemical competence of pre-transmetalation intermediates in the Suzuki-Miyaura reaction' , Angewandte Chemie, vol. 60, no. 27 , pp. 14897-14901 , doi: 10.1002/anie.202104802.

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Abstract

Palladium(II) boronates are recognized as fundamental pre-transmetalation intermediates in Suzuki–Miyaura cross-couplings. While these typically transient species have been detected and studied spectroscopically, it is conspicuous that they have never been isolated since this important reaction was discovered over forty years ago. This study reports the synthesis of a family of unprecedented arylpalladium(II) boronates that are, by design, kinetically stable at ambient temperature, both in solution and in the solid state. These properties enabled unambiguous crystallographic confirmation of their structure for the first time and their chemical competence in a Suzuki–Miyaura reaction was demonstrated.

Item Type: Article
Authors/Creators:Olding, A and Ho, CC and Canty, AJ and Lucas, NT and Horne, J and Bissember, AC
Keywords: cross-coupling, palladium boronates, Suzuki– Miyaura reaction, transmetalation
Journal or Publication Title: Angewandte Chemie
Publisher: Wiley-V C H Verlag Gmbh
ISSN: 1433-7851
DOI / ID Number: 10.1002/anie.202104802
Copyright Information:

Copyright 2021 Wiley-VCH Gmb

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