The increasing complexity of molecular targets for chemical industries, such as pharmaceutical and agricultural chemistry, necessitates the development of new reaction methods to enable syntheses that are as efficient and direct as possible. Processes that form carbon–carbon bonds, such as the Suzuki–Miyaura coupling of aryl halides and boronates employed in a number of drug syntheses, are particularly valuable in assembling the intricate carbon skeletons of these molecules. In the present work, we aim to contribute to the field of transition metal-catalyzed cross-coupling by developing a method for the nickel-catalyzed borylation of aryl <i>O</i>-sulfamates. This method would serve as an alternative to existing costly, harsh, or environmentally damaging methods to generate the boronates required for Suzuki couplings. It requires neither palladium catalysis nor Grignard chemistry, and the sulfamate substrates used are readily accessible from commercially available phenols. Furthermore, the method is broad in scope, able to produce various aryl and hetaryl boronates in reasonable yields. Our method allows for the production of boronates by relatively mild and efficient means, facilitating the use of Suzuki–Miyaura cross-coupling in the assembly of complex organic molecules.

Nickel-catalyzed borylation of aryl <i>O</i>-sulfamates

253rd National Meeting (2017)

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Nickel-catalyzed borylation of aryl O-sulfamates