Cyclic Iodine Reagents Enable Allylic Alcohols for Alkyl Boronate Addition/Rearrangement by Photoredox Catalysis1. Issue 12 (26th October 2018)

• Record Type: Journal Article
• Authors: Liu, Mingshang; Huang, Hanchu; Chen, Yiyun
• Is Part Of: Chinese journal of chemistry. Volume 36:Issue 12(2018)
• Page Start: 1209
• Page End: 1212
• Publication Date: 2018-10-26
• Subjects: allylic alcohol -- cyclic iodine reagents -- quaternary all‐carbon center -- photoredox catalysis -- alkyl boronate; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.201800461
• Languages: English
• ISSNs: 1001-604X

Abstract

Abstract: All‐carbon quaternary centers are prevalent in bioactive small molecules. However, their efficient construction remains a formidable synthetic challenge. Here we report cyclic iodine(III) reagents enable the synthesis of cyclopentanones, cyclohexanones, and dihydrofuranones bearing α‐quaternary centers by photoredox catalysis. The reaction proceeds by the formation of the novel cyclic iodine(III) reagent‐allylic alcohol complex, which enables the first alkyl boronate addition and semi‐pinacol rearrangement of allylic alcohols with dual alcohol and olefin activation. The reaction is suitable for gram scale synthesis and is transformable to alcohols, olefins, oximes, and lactones with an α‐quaternary center in one step. Abstract : Here we report cyclic iodine(III) reagents enable the synthesis of cyclopentanones, cyclohexanones, and dihydrofuranones bearing α‐quaternary centers by photoredox catalysis. The reaction proceeds by the formation of the novel cyclic iodine(III) reagent‐allylic alcohol complex, which enables the first alkyl boronate addition and semi‐pinacol rearrangement of allylic alcohols with dual alcohol and olefin activation.