Journal
TETRAHEDRON
Volume 104, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2021.132597
Keywords
Palladium; Precatalyst; Biaryl phosphine; Buchwald; Hartwig amination; Suzuki; Miyaura cross coupling
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BippyPhos shows high catalytic efficiency in Buchwald - Hartwig amination reactions. However, its wider application is limited by the lack of readily available precatalysts. In this study, we report the gram-scale synthesis and characterization of isopropylBippyPhos, and its conversion to isopropylBippyPhos Pd G2, a biaryl phosphine precatalyst. We demonstrate the competence of isopropylBippyPhos Pd G2 in palladium-catalyzed Buchwald - Hartwig amination reactions and Suzuki - Miyaura cross-coupling reactions.
A review of our high throughput reaction screening data revealed that BippyPhos was frequently associated with successful outcomes in Buchwald - Hartwig amination reactions. A barrier to the wider use of this ligand, particularly among those performing smaller scale work, may be the lack of a readily available precatalyst. We describe the multi-gram synthesis and characterization of isopropylBippyPhos, and its conversion to isopropylBippyPhos Pd G2, a biaryl phosphine precatalyst. We demonstrate the competency of isopropylBippyPhos Pd G2 in palladium catalyzed Buchwald e Hartwig amination reactions and in Suzuki e Miyaura cross coupling reactions. (C) 2021 Elsevier Ltd. All rights reserved.
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