Carboxyboronate: A Versatile C1 Building Block

Autor:	Diego B. Diaz, Andrei K. Yudin, Reed T. Larson, Chieh-Hung Tien, Aleksandra Holownia
Rok vydání:	2019
Předmět:	inorganic chemicals chemistry.chemical_classification 010405 organic chemistry Carboxylic acid chemistry.chemical_element General Chemistry General Medicine Cleavage (embryo) 010402 general chemistry Combinatorial chemistry 01 natural sciences Catalysis Ruthenium 0104 chemical sciences chemistry Nucleophile Molecule Reactivity (chemistry) Carbonylation
Zdroj:	Angewandte Chemie. 131:15292-15297
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.201907486
Popis:	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.
Databáze:	OpenAIRE
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