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

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An unconventional sulfur-to-selenium-to-carbon radical transfer: chemo-and regioselective cyclization of yne-ynamides
Green Chemistry ( IF 9.3 ) Pub Date : 2020/01/13 , DOI: 10.1039/c9gc03745d
Shubham Dutta _{1,

2,

3,

4} , B. Prabagar _{1,

2,

3,

4} , Rajeshwer Vanjari _{1,

2,

3,

4} , Vincent Gandon _{5,

6,

7,

8,

9} , Akhila K. Sahoo _{1,

2,

3,

4}

Affiliation

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.

中文翻译：

非常规的硫-硒-碳自由基转移：炔炔基酰胺的化学和区域选择性环化

罕见的硫→硒→碳自由基转移过程被用于开发史无前例的硒烯自由基介导的炔键联氨酰胺的区域选择性环化。密度泛函理论研究和HRMS实验用于建立噻吩基和硒烯基之间的反应性规模。这种转化的独特特性包括：（1）RSE的通过RS的化学选择性反应性，（2）对炔超过炔酰胺区域选择性RSE攻击，（3）5-外型-Dig炔炔酰胺的环化，以不寻常的4-硒基吡咯和（4）绿色合成方法。还描述了甲基二硒化物与炔炔基酰胺与甲基硒代吡咯的反应。

更新日期：2020-02-24

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