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. 2021 Feb 19;60(8):4342-4349.
doi: 10.1002/anie.202010211. Epub 2020 Dec 23.

Carboxyboronate as a Versatile In Situ CO Surrogate in Palladium-Catalyzed Carbonylative Transformations

Chieh-Hung Tien  1 , Alina Trofimova  1 , Aleksandra Holownia  1 , Branden S Kwak  1 , Reed T Larson  2 , Andrei K Yudin  1
Affiliations

Carboxyboronate as a Versatile In Situ CO Surrogate in Palladium-Catalyzed Carbonylative Transformations

Chieh-Hung Tien et al. Angew Chem Int Ed Engl. .

Abstract

The application of carboxy-MIDA-boronate (MIDA=N-methyliminodiacetic acid) as an in situ CO surrogate for various palladium-catalyzed transformations is described. Carboxy-MIDA-boronate was previously shown to be a bench-stable boron-containing building block for the synthesis of borylated heterocycles. The present study demonstrates that, in addition to its utility as a precursor to heterocycle synthesis, carboxy-MIDA-boronate is an excellent in situ CO surrogate that is tolerant of reactive functionalities such as amines, alcohols, and carbon-based nucleophiles. Its wide functional-group compatibility is highlighted in the palladium-catalyzed aminocarbonylation, alkoxycarbonylation, carbonylative Sonogashira coupling, and carbonylative Suzuki-Miyaura coupling of aryl halides. A variety of amides, esters, (hetero)aromatic ynones, and bis(hetero)aryl ketones were synthesized in good-to-excellent yields in a one-pot fashion.

Keywords: C1 building blocks; CO surrogates; carbonylation; carboxyboronates; palladium catalysis.

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