Transition Metal‐Free, Free‐Radical Sulfenylation of the α‐C(sp3)−H Bond in Arylacetamides and Its Application Toward 2‐Thiomethyl Benzoxazoles Synthesis

Transition Metal‐Free, Free‐Radical Sulfenylation of the α‐C(sp3)−H Bond in Arylacetamides and Its Application Toward 2‐Thiomethyl Benzoxazoles Synthesis

This paper reports the transition metal‐free C(sp3)−H sulfenylation of arylacetamides by using thiophenols as the sulfenyl reagents. The reactions take place in the presence of only K3PO4. Control experiments indicate that the reactions proceed via a featured sulfur‐centred free radical intermediate...

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Veröffentlicht in:Advanced synthesis & catalysis 2021-10, Vol.363 (19), p.4627-4631
Hauptverfasser: Tian, Shanghui, Wang, Chaoli, Xia, Jianhui, Wan, Jie‐Ping, Liu, Yunyun
Format: Artikel
Sprache:eng
Schlagworte:
Arylacetamide
C(sp3)−H bond
Chemical reactions
Free radical
Free radicals
Potassium phosphates
Reagents
Sulfenylation
Synthesis
Transition metal-free
Transition metals
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Zusammenfassung:This paper reports the transition metal‐free C(sp3)−H sulfenylation of arylacetamides by using thiophenols as the sulfenyl reagents. The reactions take place in the presence of only K3PO4. Control experiments indicate that the reactions proceed via a featured sulfur‐centred free radical intermediate. In addition, the synthesis of 2‐thiomethyl benzoxazoles has been realized via the p‐toluenesulfonic acid (p‐TSA) promoted annulation of the sulfenylated products.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100816