Directing-Group-Controlled Ring-Opening Addition and Hydroarylation of Oxa/azabenzonorbornadienes with Arenes via C–H Activation

An efficient method for the directing group controlled rhodium-catalyzed addition reaction of oxa/azabicylic alkenes with aromatic ketones and benzoic acids has been developed. The ketones and benzoic acids afforded different addition products when reacted with oxa/azabicyclic alkenes. The reaction...

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Veröffentlicht in:Organic letters 2020-05, Vol.22 (9), p.3339-3344
Hauptverfasser: Zhang, Keyang, Khan, Ruhima, Chen, Jingchao, Zhang, Xuexin, Gao, Yang, Zhou, Yongyun, Li, Kangkui, Tian, Youxian, Fan, Baomin
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Sprache:eng
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Zusammenfassung:An efficient method for the directing group controlled rhodium-catalyzed addition reaction of oxa/azabicylic alkenes with aromatic ketones and benzoic acids has been developed. The ketones and benzoic acids afforded different addition products when reacted with oxa/azabicyclic alkenes. The reaction between ketones and azabenzonorbornadienes furnished the ring-opening addition products. The reaction between benzoic acids and aza/oxabicyclic alkenes proceeded in the absence of silver salt, giving the 1:2 hydroarylation products in yields up to 96%.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00765