Carboxyboronate: A Versatile C1 Building Block.

Autor: Holownia A; Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George., Toronto, ON, M5S 3H6, Canada., Tien CH; Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George., Toronto, ON, M5S 3H6, Canada., Diaz DB; Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George., Toronto, ON, M5S 3H6, Canada., Larson RT; Process Research & Development, MRL, Merck & Co, Kenilworth, NJ, 07033, USA., Yudin AK; Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George., Toronto, ON, M5S 3H6, Canada.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2019 Oct 14; Vol. 58 (42), pp. 15148-15153. Date of Electronic Publication: 2019 Sep 10.
DOI: 10.1002/anie.201907486
Abstrakt: 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.
(© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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