We herein describe the direct Suzuki-Miyaura coupling of dan-substituted, saturated organoboron compounds. Despite its Lewis aciditydiminished character of the boron center, cyclopropyl-B(dan) can be activated by t-BuOK to undergo transmetalation with a palladium complex. The increased s-character of the CÀ B(dan) bond as compared with other alkyl-B(dan) should be the key to the reaction.
Direct, transition metal-free B(dan)-installation into organic frameworks has been developed. Heteroaryl–H bonds were transformable into the respective heteroaryl–B(dan) bonds through deprotonation. The resulting heteroaryl–B(dan) compounds, which are otherwise difficult to...
We herein describe the direct Suzuki–Miyaura coupling of dan-substituted, saturated organoboron compounds. Despite its Lewis acidity-diminished and robust character of the boron center, cyclopropyl–B(dan) can be activated by t-BuOK to under-go transmetalation with a palladium complex. The increased s-character of the C–B(dan) bond as compared with other alkyl–B(dan) should be the key to the smooth reaction.
The front cover picture illustrates a palladium catalyst smoothly producing cyclopropylarenes, like an oyster, a local specialty in Hiroshima, producing clean water. In the direct Suzuki−Miyaura coupling, dan‐substituted, Lewis acidity‐diminished cyclopropylboronamides can be activated by t‐BuOK. The increased s‐character of the cyclopropyl−B(dan) bond should be the key to transmetalation with the palladium catalyst. Details can be found in the Communication by Hiroto Yoshida and co‐workers (M. Koishi, K. Tomota, M. Nakamoto, H. Yoshida, Adv. Synth. Catal. 2023, 365, 682–686; DOI: 10.1002/adsc.202201141).
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