Friedel−Crafts Arylation Reactions of N-Sulfonyl Aldimines or Sulfonamidesulfones with Electron-Rich Arenes Catalyzed by FeCl3·6H2O: Synthesis of Triarylmethanes and Bis-heteroarylarylmethanes
摘要:
The FeCl3 center dot 6H(2)O-catalyzed Friedel-Crafts arylation reactions of N-sulfonyl aldimines or sulfonamidesulfones with electron-rich arenes and heteroarenes, which lead to the formation of triarylmethanes and bis-heteroarylarylmethanes, are developed. The use of mild reaction conditions, low catalytic loading, high yield, and single step synthesis are the advantages of the present procedure.
A rapid, highly efficient, and general protocol for the synthesis of functionalized triarylmethanes: a straightforward access for the synthesis of (−)-tatarinoid C
作者:B. Madhu Babu、Pramod B. Thakur、N. Nageswara Rao、G. Santosh Kumar、H.M. Meshram
DOI:10.1016/j.tetlet.2014.01.107
日期:2014.3
functionalized triarylmethane is described by the Friedel–Crafts alkylation of methoxybenzenes with a variety of aldehydes in the presence of BF3·OEt2. The generality of the method is demonstrated by screening a variety of di- or tri-substituted arenes as well as substituted aromatic, heteroaromatic, and aliphatic aldehydes. (−)-Tatarinoid C is synthesized in a single step following the same protocol.
Cationic ruthenium porphyrin complex was found to be an efficient catalyst for the Friedel-Crafts type reaction of arenes with imines. The use of a structurally rigid tetradentate porphyrin as the equatorial ligand and weakly coordinating axial ligand is the key to bring out the catalytic reactivity of ruthenium for the reaction.