Synfacts 2006(1): 0017-0017  
DOI: 10.1055/s-2005-921685
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

A Benzyne Route to Xanthones and Thioxanthones

Contributor(s): Victor Snieckus, Robert Engqvist
J. Zhao, R. C. Larock*
Iowa State University, USA
Further Information

Publication History

Publication Date:
16 December 2005 (online)

Significance

A tandem reaction of salicylic esters and thiosalicylic esters with in situ benzyne, generated from the reaction of o-(trimethylsilyl)phenyl triflate with CsF, leads to the formation of xanthones and thioxanthones from readily available starting materials in reasonable to good yields. The conditions are mild and the regioselectivity, as evidenced in the formation of relevant xanthones (R1, R4, R5 = H, R3 = OMe), is high.