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Published on: September 8, 2013
Electrochemical Allylic C(sp3)-H Isothiocyanation via [3,3]-Sigmatropic Rearrangement
Xuezhuang Gao1, Hui He2, Kaili Miao1
1College of Chemistry & Molecular Engineering, Qingdao University of Science & Technology, 53 Zhengzhou Road, 266042 Qingdao, P. R. China.
Abstract:
The direct allylic C(sp3)-H functionalization provides a straightforward protocol for the synthesis of valuable molecules. We report herein the first chemo- and site-selective method for allylic C(sp3)-H isothiocyanation of various internal alkenes under mild electrochemical conditions. This method exhibits broad functional group tolerance and excellent selectivity and can be applied for late-stage isothiocyanation of bioactive molecules. Combined experimental and computational studies indicate that the reaction proceeds via an unexpected [3,3]-sigmatropic rearrangement.
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