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

Citation

Olding, A and Ho, CC and Canty, AJ and Lucas, NT and Horne, J and Bissember, AC, Synthesis of arylpalladium(II) boronates: confirming the structure and chemical competence of pre-transmetalation intermediates in the Suzuki-Miyaura reaction, Angewandte Chemie, 60, (27) pp. 14897-14901. ISSN 1433-7851 (2021) [Refereed Article]

Copyright Statement

Copyright 2021 Wiley-VCH Gmb

DOI: doi:10.1002/anie.202104802

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 Details

Item Type:Refereed Article
Keywords:cross-coupling, palladium boronates, Suzuki– Miyaura reaction, transmetalation
Research Division:Chemical Sciences
Research Group:Organic chemistry
Research Field:Organic chemical synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:Olding, A (Mr Angus Olding)
UTAS Author:Ho, CC (Dr Curtis Ho)
UTAS Author:Canty, AJ (Professor Allan Canty)
UTAS Author:Horne, J (Dr James Horne)
UTAS Author:Bissember, AC (Associate Professor Alex Bissember)
ID Code:144905
Year Published:2021
Funding Support:Australian Research Council (DP200101714)
Deposited By:Chemistry
Deposited On:2021-06-20
Last Modified:2021-08-18
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