Synthesis of Thioxanthones through Formal C–H Thiolation of Benzoic Acid Esters and Acid-mediated Direct Cyclization

An efficient thioxanthone synthesis from benzoic acid esters is disclosed. Various thioxanthones were prepared by iridium-catalyzed C–H borylation of benzoic acid esters followed by copper-catalyzed deborylthiolation and direct acid-mediated cyclization. We also achieved a synthesis of benzo-fused t...

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Bibliographic Details
Published in:Chemistry letters 2020-07, Vol.49 (7), p.753-756
Main Authors: Mutsuura, Kotaro, Sakata, Yuki, Uchida, Keisuke, Hosoya, Takamitsu, Yoshida, Suguru
Format: Article
Language:English
Subjects:
Acids
Benzoic acid
Catalytic C-H Activation
Esters
Iridium
Thioxanthenone
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Summary:An efficient thioxanthone synthesis from benzoic acid esters is disclosed. Various thioxanthones were prepared by iridium-catalyzed C–H borylation of benzoic acid esters followed by copper-catalyzed deborylthiolation and direct acid-mediated cyclization. We also achieved a synthesis of benzo-fused thioxanthones through a transformation of an aryne intermediate having an ester moiety.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.200190