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Synfacts 2018; 14(11): 1199
DOI: 10.1055/s-0037-1611269
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Cobalt-Catalyzed Regioselective Photochemical Synthesis of 1H-Tetrazoles

Contributor(s):
Yasuhiro Uozumi
,
Yuya Sugiyama
Verma F, Sahu A, Singh PK, Rai A, Singh M, Rai VK. * Guru Ghasidas Vishwavidyalaya, Bilaspur and Jawaharlal Nehru University, New Delhi, India
Visible-Light Driven Regioselective Synthesis of 1H-Tetrazoles from Aldehydes through Isocyanide-Based [3+2] Cycloaddition.

Green Chem. 2018;
20: 3783-3789
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Publication History

Publication Date:
18 October 2018 (online)

 
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Key words

cobalt catalysis - photocatalysis - tetrazoles - graphitic carbon nitride - aldehydes - cycloaddition

Significance

A cobalt-doped polymeric graphitic carbon nitride catalyst (Co@g-C3N4) was prepared by calcination of urea followed by treatment with Co(OAc)2·4H2O in aqueous methanol (eq. 1). Co@g-C3N4 catalyzed the reaction of aldehydes with sodium azide under visible-light irradiation and air to give the corresponding 5-substituted 1H-tetrazoles in up to 95% yield (eq. 2). The authors propose an isocyanide intermediate, formed through a Co@g-C3N4-induced photocatalytic 1,2-phenyl migration from C to N.


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Comment

Co@g-C3N4 was characterized by means of SEM, XPS, XRD, FTIR, UV-Vis, EDX, TEM, and photoluminescence analyses. In the ­reaction of 4-chlorobenzaldehyde with sodium azide, the catalyst was recovered by filtration and reused four times without significant loss of its catalytic activity.


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