%0 Journal Article
%A Singh, Parvinder Pal
%A Aithagani, Sravan Kumar
%A Yadav, Mahipal
%A Singh, Varun Pratap
%A Vishwakarma, Ram A.
%D 2016
%T 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
%U https://acs.figshare.com/articles/journal_contribution/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/2433886
%R 10.1021/jo302797r.s001
%2 https://ndownloader.figshare.com/files/4076425
%K Total Synthesis
%K Innate
%K quinoxaline
%K flask conditions
%K Application
%K arylboronic acids
%K Functionalization
%K synthesis
%K heterocylce
%K acetylacetonate
%K Heterocycle
%K application
%K functionalization
%K organoboron species
%K K 2S
%K heterocycle
%K Organoboron Species
%K Quinone
%K Pyrazine Alkaloid Botryllazine AHere
%K isoquinoline
%K Optimized conditions
%K pyridine
%K catalyst
%K oxidant
%K anticancer marine pyrazine alkaloid botryllazine
%K quinone
%K yield
%K quinoline
%K monoarylated products
%K TBAB
%X Here,
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.
%I ACS Publications