Synthesis of allenyl-B(MIDA) via hydrazination/fragmentation reaction of B(MIDA)-propargylic alcohol

Allenylboronates represent a very intriguing class of organoborons but are challenging to synthesis. In addition, these compounds are typically unstable, rendering the separation difficult. We report herein a practical and concise route to a new class of stable, easy-separable allenyl B(MIDA) via a hydrazina-tion/fragmentation of B(MIDA)-propargylic alcohols. The synthesis of optically active allenyl B(MIDA) was also achieved. Interesting reactivity of the resulting product was observed.(c) 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

Automated summary

Allenylboronates are an intriguing class of organoborons that are challenging to synthesize and typically unstable, making separation difficult. This study presents a practical and concise route to a new class of stable and easily separable allenyl B(MIDA) through hydrazination/fragmentation of B(MIDA)-propargylic alcohols. The synthesis of optically active allenyl B(MIDA) was also achieved, and interesting reactivity of the resulting product was observed.