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Metal- and base-free regioselective thiolation of the methyl C(sp3)–H bond in 2-picoline N-oxides

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Abstract

A one-pot, two-step synthesis of pyridine-2-ylmethyl thioethers is developed through a TFAA-mediated [3,3]-sigmatropic rearrangement of pyridine N-oxides and TBAB-catalyzed direct conversion of trifluoroacetates into thioethers under metal- and base-free conditions. This methodology enables thiolation of the unactivated methyl C(sp3)–H bond in 2-picolines with thiols. Remarkable features of the method include high regioselectivity, step- and atom-economy, mild conditions, simple operation, wide substrate scope and scalability. Furthermore, the method has been successfully applied to the synthesis of omeprazole sulfide and rabeprazole sulfide without the need for TBAB catalysis. A comprehensive green chemistry metrics analysis indicated that this method is much more efficient and greener than the reported synthesis of rabeprazole sulfide.

Graphical abstract: Metal- and base-free regioselective thiolation of the methyl C(sp3)–H bond in 2-picoline N-oxides

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Publication details

The article was received on 01 Oct 2018, accepted on 20 Nov 2018 and first published on 21 Nov 2018


Article type: Paper
DOI: 10.1039/C8GC03072C
Citation: Green Chem., 2019, Advance Article
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    Metal- and base-free regioselective thiolation of the methyl C(sp3)–H bond in 2-picoline N-oxides

    D. Wang, Z. Liu, Z. Wang, X. Ma and P. Yu, Green Chem., 2019, Advance Article , DOI: 10.1039/C8GC03072C

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