Ortho Arylation of N-Aryl Amides and the Construction of Diagonal Tetraaryl Anilides via BBr3-Derived Dibromobora-cycles

06 February 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


In this study, we present a first comprehensive palladium-catalyzed Suzuki–Miyaura C(sp2)-C(sp2) cross-coupling reaction, employing newly derived di-bromo-boracycles as pivotal reagents for the synthesis of ortho arylated N-aryl amides. Our research hinges on the utilization of di-bromo-boracycles, which act as temporary reservoirs of boron, facilitating subsequent transformations in cross-coupling reaction. The di-bromo-boracycle offers a unique opportuni-ty for regioselective carbon-carbon bond formation to the ortho position of N-aryl amides. This mild, site-specific, and scalable protocol is compatible with a wide array of easily accessible functionalized anilides and aryl iodides, as demonstrated by 55 examples, yielding products in the range of 30%-95%. Furthermore, the methodology trans-cends conventional practices, enabling the construction of previously unattainable diagonal aryl systems, highlighting the exceptional potential of our approach for accessing intricate molecular architectures.


C-H activation


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