Cascade Multicomponent Assemblies Involving 1,3-Enynes via Auto-Tandem Palladium Catalysis
Ze-Liang He1, Yi Zhang1, Zhi-Chao Chen1
1Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Abstract:
Here we report a three-component auto-tandem reaction of 1,3-enyne-tethered carbonyls, organoboronic reagents, and suitable nucleophiles catalyzed by palladium, proceeding through consecutive intramolecular vinylogous addition, Suzuki coupling, and allylic alkylation. This process exhibited high chemo- and regioselectivity with 1,3,4-trifunctionalization of the 1,3-enyne motif, and a wide range of 2H-chromenes, 1,2-dihydroquinolines, benzo[b]oxepines, 1,7-annulated indoles, and other frameworks were efficiently constructed in fair to good yields and E/Z selectivity.
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