Iodine-Mediated Domino Oxidative Cyclization: One-Pot Synthesis of 1,3,4-Oxadiazoles via Oxidative Cleavage of C(sp(2))-H or C(sp)-H Bond

Yuxing Fan; Yongqin He; Xingxing Liu; Ting Hu; Haojie Ma; Xiaodong Yang; Xinliang Luo; Guosheng Huang

doi:10.1021/acs.joc.6b01135

Iodine-Mediated Domino Oxidative Cyclization: One-Pot Synthesis of 1,3,4-Oxadiazoles via Oxidative Cleavage of C(sp(2))-H or C(sp)-H Bond

J Org Chem. 2016 Aug 5;81(15):6820-5. doi: 10.1021/acs.joc.6b01135. Epub 2016 Jul 21.

Authors

Yuxing Fan^{1

2}, Yongqin He^{1

2}, Xingxing Liu^{1

2}, Ting Hu^{1

2}, Haojie Ma^{1

2}, Xiaodong Yang^{1

2}, Xinliang Luo^{1

2}, Guosheng Huang^{1

2}

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou, Gansu, 730000, P. R. China.
² Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province , Lanzhou, 730000, P. R. China.

PMID: 27387390
DOI: 10.1021/acs.joc.6b01135

Abstract

An I2-promoted, metal-free domino protocol for one-pot synthesis of 1,3,4-oxadiazoles has been developed via oxidative cleavage of C(sp(2))-H or C(sp)-H bonds, followed by cyclization and deacylation. In this reaction, the use of K2CO3 as a base is found to be an essential factor in the cyclization and the C-C bond cleavage. This procedure proceeded smoothly in moderate to high yields with good functional group compatibility.