Acylboronates in Polarity-Reversed Generation of Acyl Palladium(II) Intermediates

Alina Trofimova; Aleksandra Holownia; Chieh-Hung Tien; Martynas J Širvinskas; Andrei K Yudin

doi:10.1021/acs.orglett.1c00742

Acylboronates in Polarity-Reversed Generation of Acyl Palladium(II) Intermediates

Org Lett. 2021 May 7;23(9):3294-3299. doi: 10.1021/acs.orglett.1c00742. Epub 2021 Apr 13.

Authors

Alina Trofimova¹, Aleksandra Holownia¹, Chieh-Hung Tien¹, Martynas J Širvinskas¹, Andrei K Yudin¹

Affiliation

¹ Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada.

PMID: 33848176
DOI: 10.1021/acs.orglett.1c00742

Abstract

We report a catalytic cross-coupling process between aryl (pseudo)halides and boron-based acyl anion equivalents. This mode of acylboronate reactivity represents polarity reversal, which is supported by the observation of tetracoordinated boronate and acyl palladium(II) species by ¹¹B, ³¹P NMR, and mass spectrometry. A broad scope of aliphatic and aromatic acylboronates has been examined, as well as a variety of aryl (pseudo)halides.