Issue 3, 2015

Deuterative cyclization of sulfanyl 1,6-diynes: complete and monodeuteration of functional groups on heterocycles

Abstract

Regioselective H/D exchange reaction of functional groups on heterocycles proceeded via a transition metal-free reductive cyclization of sulfanyl 1,6-diynes using sodium borodeuteride/ethanol-D1. Both alkoxide- and aryloxide-mediated cyclizations and amination–cyclization resulted in the deuteration of functional groups with high deuterium incorporation. Reductive cyclization using sodium borodeuteride/ethanol exclusively afforded the monodeuterated furans and pyrroles in good yields.

Graphical abstract: Deuterative cyclization of sulfanyl 1,6-diynes: complete and monodeuteration of functional groups on heterocycles

Supplementary files

Article information

Article type
Research Article
Submitted
17 dec 2014
Accepted
09 jan 2015
First published
20 jan 2015

Org. Chem. Front., 2015,2, 201-205

Author version available

Deuterative cyclization of sulfanyl 1,6-diynes: complete and monodeuteration of functional groups on heterocycles

Y. Ito and M. Yoshimatsu, Org. Chem. Front., 2015, 2, 201 DOI: 10.1039/C4QO00333K

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