Rh(III)‐Catalyzed Divergent C2‐carboxymethylation of Indoles and C7‐formylmethylation of Indolines with Vinylene Carbonate. Issue 10 (27th September 2021)

• Record Type: Journal Article
• Authors: Hu, Weinan; Wang, Xu; Yu, Xiaoni; Zhu, Xinju; Hao, Xin‐Qi; Song, Mao‐Ping
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 10(2021)
• Page Start: 2557
• Page End: 2561
• Publication Date: 2021-09-27
• Subjects: rhodium-catalyzed -- indoles -- indolines -- vinyl carbonate -- three-component; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202100515
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: A Rh‐catalyzed divergent alkylation of indole derivatives with vinyl carbonate was described. Depending on the substrate and solvent, indoles reacted with vinyl carbonate and alcohols to give C2 carboxymethylated adducts via a sequential three‐component reaction, while indolines reacted with vinyl carbonate in toluene to provide C7 formylmethylated products. The structures of carboxymethylated product 3 a and formylmethylated product 5 a were further confirmed by X‐ray analysis. The current protocol featured broad substrate scope, tunable reaction conditions, divergent functionalization, and good regioselectivity. Abstract : A Rh‐catalyzed C2‐carboxymethylation of indoles in alcohols and C7‐formylmethylation of indolines in toluene with vinylene carbonate has been successfully developed.