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J Org Chem. 2013 Mar 15;78(6):2639-48. doi: 10.1021/jo302797r. Epub 2013 Feb 27.

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.

Author information

1
Medicinal Chemistry Division, Indian Institute of Integrative Medicine (Council of Scientific & Industrial Research), Jammu 180 001, India. ppsingh@iiim.res.in

Abstract

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.

PMID:
23419207
DOI:
10.1021/jo302797r
[Indexed for MEDLINE]

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