Protocol for the synthesis of homoallenic alcohols via allenyl radical-mediated allenylation of alkenes

Homoallenic alcohols are versatile building blocks to access complex molecules in synthetic chemistry. We present a protocol for accessing homoallenic alcohols by an allenyl radical-involved radical-polar crossover process. We describe steps for preparing solvents and the photoreactor and synthesizing 5-methyl-1-phenyl-3-tosylhexa-3,4-dien-1-ol 3 in 85% yield. In addition, 5-methyl-1-phenyl-3-tosylhexa-3,4-dien-1-ol 3 has been successfully synthesized in 2-mmol scale. This protocol is also applicable to the synthesis of homoallenic amides.For complete details on the use and execution of this protocol, please refer to Wei et al. (2023).1

Automated summary

Homoallenic alcohols are versatile building blocks in synthetic chemistry. We present a protocol for their synthesis using an allenyl radical-involved radical-polar crossover process, and successfully prepare 5-methyl-1-phenyl-3-tosylhexa-3,4-dien-1-ol.