Palladium‐Catalyzed Ring‐Opening Addition of Activated Vinyl Cyclopropanes with N‐Tosylhydrazones. Issue 7 (26th January 2023)

• Record Type: Journal Article
• Authors: Wang, Yiding; Shen, Lei; Wang, Helin; Luo, Yixin; Zeng, Qingle
• Is Part Of: European journal of organic chemistry. Volume 26:Issue 7(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-01-26
• Subjects: Vinyl cyclopropanes -- Catalysis -- Palladium -- Ring-opening -- Tosylhydrazones; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200942
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Ring‐opening addition reaction of activated vinyl cyclopropanes with N ‐tosylhydrazones in the presence of palladium(0) and triphenylphosphine affords N ‐tosylhydrazone butenylmalonate compounds. Aromatic aldehyde‐derived N ‐tosylhydrazones produced terminal and internal N ‐allylated products, in which the terminal products are the main. While ketone‐derived tosylhydrazones produced only terminal addition products. The transformation relationship of the terminal and internal N ‐allylated products in the reaction was also observed. A reasonable mechanism is proposed based on preliminary experimental results. Abstract : Palladium‐catalyzed ring‐opening addition reaction of activated vinyl cyclopropanes with N ‐tosylhydrazones provides N ‐tosylhydrazone butenylmalonate compounds in good yields. Aromatic aldehyde‐derived N ‐tosylhydrazones produced terminal and internal N ‐allylated products, in which the terminal products are the main. While ketone‐derived tosylhydrazones produced only terminal addition products.