Tien, Chieh-Hung; Trofimova, Alina; Holownia, Aleksandra; Kwak, Branden S.; Larson, Reed T.; Yudin, Andrei K. published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Carboxyboronate as a Versatile In Situ CO Surrogate in Palladium-Catalyzed Carbonylative Transformations》.Formula: C7H5BrO2 The article contains the following contents:
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, alcs., 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. The experimental part of the paper was very detailed, including the reaction process of 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4Formula: C7H5BrO2)
Furthermore, the coupling of 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4) with β-methallyl alcohol was catalyzed by Pd(OAc)2 in combination with P(t-Bu)3.Formula: C7H5BrO2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary