Cascade C-H Annulation of Aldoximes with Alkynes Using O 2 as the Sole Oxidant: One-Pot Access to Multisubstituted Protoberberine Skeletons

A cascade double C-H annulation of aldoximes with alkynes to produce benz[a]acridizinium salts is developed by using a simple catalytic system of [Cp*Rh(OAc) ] in the presence of Zn(OTf) with oxygen as the sole oxidant. In addition, the challenging C-H annulation of aldoximes with alkynes, especiall...

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Bibliographic Details
Published in:Organic letters 2017-02, Vol.19 (3), p.604-607
Main Authors: Tang, Junbin, Li, Shiqing, Liu, Zheng, Zhao, Yinsong, She, Zhijie, Kadam, Vilas D, Gao, Ge, Lan, Jingbo, You, Jingsong
Format: Article
Language:English
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Summary:A cascade double C-H annulation of aldoximes with alkynes to produce benz[a]acridizinium salts is developed by using a simple catalytic system of [Cp*Rh(OAc) ] in the presence of Zn(OTf) with oxygen as the sole oxidant. In addition, the challenging C-H annulation of aldoximes with alkynes, especially arylalkynes, to synthesize 1H-isoquinolines is also achieved under slightly modified conditions. This protocol provides an efficient one-pot access to multisubstituted dehydroberberinium skeletons from simple starting materials, which can be easily transformed into berberinium and tetrahydroberberine skeletons by controlled hydrogenation.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b03772