Synthesis of Dibenzo[c,e]oxepin-5(7H)-ones from Benzyl Thioethers and Carboxylic Acids: Rhodium-Catalyzed Double CH Activation Controlled by Different Directing Groups

A rhodium(III)‐catalyzed cross‐coupling of benzyl thioethers and aryl carboxylic acids through the two directing groups is reported. Useful structures with diverse substituents were efficiently synthesized in one step with the cleavage of four bonds (CH, CS, OH) and the formation of two bonds (C...

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Bibliographic Details
Published in:Angewandte Chemie 2015-04, Vol.127 (18), p.5568-5572
Main Authors: Zhang, Xi-Sha, Zhang, Yun-Fei, Li, Zhao-Wei, Luo, Fei-Xian, Shi, Zhang-Jie
Format: Article
Language:English
Subjects:
Activation
Aromatic compounds
Biocompatibility
C-H-Aktivierung
Carbonsäuren
Carboxylic acids
Cleavage
Coupling (molecular)
Formations
Kreuzkupplungen
Rhodium
Selectivity
Synthesemethoden
Synthesis
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Summary:A rhodium(III)‐catalyzed cross‐coupling of benzyl thioethers and aryl carboxylic acids through the two directing groups is reported. Useful structures with diverse substituents were efficiently synthesized in one step with the cleavage of four bonds (CH, CS, OH) and the formation of two bonds (CC, CO). The formed structure is the privileged core in natural products and bioactive molecules. This work highlights the power of using two different directing groups to enhance the selectivity of a double CH activation, the first of such examples in cross‐oxidative coupling. Doppelkreuz: In der Rhodium(III)‐katalysierten doppelten C‐H‐Kreuzkupplung zwischen Benzylthioethern und Carbonsäuren erhöhen die beiden dirigierenden Gruppen (DGs) die Selektivität der doppelten C‐H‐Aktivierung. Eine DG wird in das Produkt eingebaut, die andere wird in situ abgespalten.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201500486