Cp*Co(III)‐Catalyzed C−H Alkenylation of Aromatic Ketones with Alkenes. Issue 3 (28th November 2018)

• Record Type: Journal Article
• Authors: Sk, Md Raja; Bera, Sourav Sekhar; Maji, Modhu Sudan
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 3(2019)
• Page Start: 585
• Page End: 590
• Publication Date: 2018-11-28
• Subjects: cobalt(III)-catalyzed -- ketone-directed -- C−H alkenylation -- cinnamic acids -- indanone and indenone; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201801385
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Cost‐effective and air‐stable high‐valent cobalt(III)‐catalyzed weakly coordinating, ketone‐directed regioselective mono‐alkenylation of arenes and heteroarenes with alkenes is demonstrated. Various electron‐rich and electron‐deficient arenes are tolerated under the reaction conditions, providing E ‐alkenylated products exclusively. The tert ‐butyl‐acrylates serve as an acrylic acid surrogate to provide cinnamic acid derivatives via direct C−H alkenylation. A two‐step synthesis of a γ ‐PPAR antagonist, the synthesis of indanone, and the modification of divinylsulfone are reported as applications. The mechanistic details suggest a base‐assisted intermolecular electrophilic substitution reaction pathway. Abstract :