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

Yunlong Wei; Chen Zhu

doi:10.1016/j.xpro.2023.102598

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

STAR Protoc. 2023 Dec 15;4(4):102598. doi: 10.1016/j.xpro.2023.102598. Epub 2023 Sep 26.

Authors

Yunlong Wei¹, Chen Zhu²

Affiliations

¹ Institute of Life Science and Green Development, College of Life Science, Hebei University, Baoding 071002, China. Electronic address: ylwei@hbu.edu.cn.
² Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China. Electronic address: chzhu@sjtu.edu.cn.

Abstract

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.

Keywords: chemistry; energy; material sciences.

MeSH terms

Alcohols*
Alkenes*
Amides

Substances

Alcohols
Alkenes
Amides