A lutidine-promoted photoredox catalytic atom-transfer radical cyclization reaction for the synthesis of 4-bromo-3,3-dialkyl-octahydro-indol-2-ones

Quan-Sheng Zhao; Guo-Qiang Xu; Ji-Tao Xu; Zhu-Yin Wang; Peng-Fei Xu

doi:10.1039/c9cc09876c

A lutidine-promoted photoredox catalytic atom-transfer radical cyclization reaction for the synthesis of 4-bromo-3,3-dialkyl-octahydro-indol-2-ones

Chem Commun (Camb). 2020 Feb 18;56(14):2206-2209. doi: 10.1039/c9cc09876c. Epub 2020 Jan 24.

Authors

Quan-Sheng Zhao¹, Guo-Qiang Xu², Ji-Tao Xu², Zhu-Yin Wang², Peng-Fei Xu²

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China. xupf@lzu.edu.cn and Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P. R. China.
² State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China. xupf@lzu.edu.cn.

PMID: 31976501
DOI: 10.1039/c9cc09876c

Abstract

Reported herein is a visible-light-catalyzed photoredox atom-transfer radical cyclization (ATRC) halo-alkylation of 1,6-dienes with α-halo-ketones as the ATRC reagent. This process exhibits high atom economy, high step economy, and high redox economy, which can directly construct a 4-bromo-3,3-dialkyl-octahydro-indol-2-one core under mild conditions in one pot, and lutidine is found to be the key promoter for this ATRC process.