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Angew Chem Int Ed Engl. 2019 Aug 2. doi: 10.1002/anie.201907486. [Epub ahead of print]

Carboxyboronate: A Versatile C1-Building Block.

Author information

1
University of Toronto, Department of Chemistry, 80 St. George Street, M5S 3H6, Toronto, CANADA.
2
32-4101 Westminster Pl., L4W 4X4, Canada, Mississauga, CANADA.
3
CANADA.
4
UNITED STATES.

Abstract

The synthesis and applications of carboxy-MIDA-boronate, a novel C1 building block, are described. This molecule is accessible via a ruthenium tetraoxide-mediated cleavage of commercially available ethynyl-MIDA-boronate. In the course of this study, carboxy-MIDA-boronate was found to possess ambident reactivity towards nucleophiles. Carboxylic acid derivatization produces a broad range of previously unknown carbamoyl-, oxycarbo- and thiocarboboronates. Carboxy-MIDA-boronate and its derivatives undergo condensations to access borylated heterocycles with boron at positions that are difficult to access using alternate methods. The resulting heterocycles participate in the Suzuki-Miyaura cross-coupling reaction, enabling entry into diverse bis(heteroaryl) motifs. The carbon monoxide-releasing capacity of carboxy-MIDA-boronate was also examined and applied in palladium-catalyzed carbonylation.

KEYWORDS:

C1 building block; ambident electrophile; carboxyboronate; cross-coupling; heterocycles

PMID:
31376232
DOI:
10.1002/anie.201907486

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