title: Cascade C-H Annulation of Aldoximes with Alkynes Using O2as the Sole Oxidant: One-Pot Access to Multisubstituted Protoberberine Skeletons.
abstract: 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)2]2in the presence of Zn(OTf)2with 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.
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University , 29 Wangjiang Road, Chengdu 610064, P.R. China.
authors.forename: Junbin
authors.initials: J
authors.lastname: Tang
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University , 29 Wangjiang Road, Chengdu 610064, P.R. China.
authors.forename: Shiqing
authors.initials: S
authors.lastname: Li
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University , 29 Wangjiang Road, Chengdu 610064, P.R. China.
authors.forename: Zheng
authors.initials: Z
authors.lastname: Liu
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University , 29 Wangjiang Road, Chengdu 610064, P.R. China.
authors.forename: Yinsong
authors.initials: Y
authors.lastname: Zhao
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University , 29 Wangjiang Road, Chengdu 610064, P.R. China.
authors.forename: Zhijie
authors.initials: Z
authors.lastname: She
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University , 29 Wangjiang Road, Chengdu 610064, P.R. China.
authors.forename: Vilas D
authors.initials: VD
authors.lastname: Kadam
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University , 29 Wangjiang Road, Chengdu 610064, P.R. China.
authors.forename: Ge
authors.identifier: 0000-0001-9980-7311
authors.initials: G
authors.lastname: Gao
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University , 29 Wangjiang Road, Chengdu 610064, P.R. China.
authors.forename: Jingbo
authors.initials: J
authors.lastname: Lan
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University , 29 Wangjiang Road, Chengdu 610064, P.R. China.
authors.forename: Jingsong
authors.identifier: 0000-0002-0493-2388
authors.initials: J
authors.lastname: You