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Issue 4, 2020
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An unconventional sulfur-to-selenium-to-carbon radical transfer: chemo-and regioselective cyclization of yne-ynamides

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Abstract

An uncommon sulfur → selenium → carbon radical transfer process is employed to develop an unprecedented selenyl radical-mediated regioselective cyclization of yne-tethered-ynamides. Density functional theory studies and HRMS experiments are used to establish a reactivity scale between thiyl and selenyl radicals. The unique features of this transformation include, (1) the chemoselective reactivity of RSe˙ over RS˙, (2) regioselective RSe˙ attack on alkyne over ynamide, (3) 5-exo-dig cyclization of yne-ynamide to unusual 4-selenyl-pyrroles, and (4) the green synthetic method. The reaction of methyldiselenide with yne-ynamides to methylselenopyrroles is also described.

Graphical abstract: An unconventional sulfur-to-selenium-to-carbon radical transfer: chemo-and regioselective cyclization of yne-ynamides

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Article information


Submitted
31 Oct 2019
Accepted
09 Jan 2020
First published
13 Jan 2020

Green Chem., 2020,22, 1113-1118
Article type
Communication

An unconventional sulfur-to-selenium-to-carbon radical transfer: chemo-and regioselective cyclization of yne-ynamides

S. Dutta, B. Prabagar, R. Vanjari, V. Gandon and A. K. Sahoo, Green Chem., 2020, 22, 1113
DOI: 10.1039/C9GC03745D

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