Catalytic Borylation using an Air-Stable Zinc Boryl Reagent: Systematic Access to Elusive Acylboranes

Jesús Campos; Simon Aldridge

doi:10.1002/anie.201507627

Catalytic Borylation using an Air-Stable Zinc Boryl Reagent: Systematic Access to Elusive Acylboranes

Angew Chem Int Ed Engl. 2015 Nov 16;54(47):14159-63. doi: 10.1002/anie.201507627. Epub 2015 Sep 28.

Authors

Jesús Campos¹, Simon Aldridge²

Affiliations

¹ Inorganic Chemistry Laboratory, Dept. of Chemistry, University of Oxford, South Parks Rd, Oxford (UK) OX1 3QR. jesus.camposmanzano@chem.ox.ac.uk.
² Inorganic Chemistry Laboratory, Dept. of Chemistry, University of Oxford, South Parks Rd, Oxford (UK) OX1 3QR. simon.aldridge@chem.ox.ac.uk.

PMID: 26411884
DOI: 10.1002/anie.201507627

Abstract

The use of borylzinc reagents in palladium-catalyzed borylation chemistry is described (i.e. a boron analogue of the Negishi coupling), including a one-pot bench-top protocol using an air- and moisture-stable bis(boryl)zinc reagent. The steric/electronic properties of the boryl fragment employed enable a systematic method for accessing acylboranes, a rare class of organoboron species with great potential in chemical synthesis. The reactions proceed under mild conditions, use inexpensive commercial sources of palladium, and demonstrate a remarkable functional-group tolerance.

Keywords: boron; borylation; palladium; structure elucidation; zinc.

Publication types

Research Support, Non-U.S. Gov't