Practical Synthesis of Halogenated N‐Heterocycles via Electrochemical Anodic Oxidation of Unactivated Alkenes. Issue 42 (10th November 2021)

• Record Type: Journal Article
• Authors: He, Yanyang; Qin, Xiaowen; He, Xinxu; Wu, Xiao‐Feng; Yin, Zhiping
• Is Part Of: European journal of organic chemistry. Issue 42(2021)
• Page Start: 5831
• Page End: 5834
• Publication Date: 2021-11-10
• Subjects: Alkenes -- Anodic oxidation -- Amination -- Electrochemistry -- Nitrogen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202101189
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A general and efficient intramolecular halo‐amination of unactivated alkenes for the synthesis of various halogenated N ‐heterocycles was developed via electrochemical anodic oxidation. This protocol proceeds in a simple undivided cell by employing LiI or LiBr as redox mediums and halogen sources. A wide range of halogenated N ‐heterocycles, including three‐, five‐, and six‐membered N ‐heterocycles were constructed in moderate to good yields at room temperature. Notably, this electrochemical oxidative transformation avoids the utilization of external oxidants and strong bases, therefore represents an environmentally benign approach. Abstract : A general and efficient intramolecular halo‐amination of unactivated alkenes for the synthesis of various halogenated N ‐heterocycles was developed via electrochemical anodic oxidation. This protocol proceeds in a simple undivided cell by employing LiI or LiBr as redox mediums and halogen sources. A wide range of halogenated N ‐heterocycles, including three‐, five‐, and six‐membered N ‐heterocycles were constructed in moderate to good yields at room temperature. Notably, this electrochemical oxidative transformation avoids the utilization of external oxidants and strong bases, therefore represents an environmentally benign approach.