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Issue 1, 2019
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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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Supplementary files

Article information


Submitted
01 Oct 2018
Accepted
20 Nov 2018
First published
21 Nov 2018

Green Chem., 2019,21, 157-163
Article type
Paper

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, 21, 157
DOI: 10.1039/C8GC03072C

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