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Iron-catalyzed Cross-Coupling of Electron-Deficient Heterocycles and Quinone with Organoboron Species via Innate C–H Functionalization: Application in Total Synthesis of Pyrazine Alkaloid Botryllazine A
journal contribution
posted on 2016-02-19, 17:39 authored by Parvinder Pal Singh, Sravan Kumar Aithagani, Mahipal Yadav, Varun Pratap Singh, Ram A. VishwakarmaHere,
we report an iron-catalyzed cross-coupling reaction
of electron-deficient heterocycles and quinone with organoboron species
via innate C–H functionalization. Iron(II) acetylacetonate
along with oxidant (K2S2O8) and phase-transfer
catalyst (TBAB) under open flask conditions efficiently catalyzed
the cross-coupling of pyrazine with arylboronic acids
and gave monoarylated products in good to excellent yields. Optimized
conditions also worked for other heterocylces such as quinoxalines,
pyridines, quinoline, and isoquinoline as well as quinones. In addition,
we demonstrated as a first example its application for the synthesis
of anticancer marine pyrazine alkaloid botryllazine A.
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Keywords
Total SynthesisInnatequinoxalineflask conditionsApplicationarylboronic acidsFunctionalizationsynthesisheterocylceacetylacetonateHeterocycleapplicationfunctionalizationorganoboron speciesK 2SheterocycleOrganoboron SpeciesQuinonePyrazine Alkaloid Botryllazine AHereisoquinolineOptimized conditionspyridinecatalystoxidantanticancer marine pyrazine alkaloid botryllazinequinoneyieldquinolinemonoarylated productsTBAB
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