74346-22-8Relevant articles and documents
Electrochemical Semipinacol Rearrangements of Allylic Alcohols: Construction of All-Carbon Quaternary Stereocenters
Kang, Jun-Chen,Tu, Yong-Qiang,Dong, Jia-Wei,Chen, Chao,Zhou, Jia,Ding, Tong-Mei,Zai, Jian-Tao,Chen, Zhi-Min,Zhang, Shu-Yu
, p. 2536 - 2540 (2019)
The first examples of electrochemical trifluoromethylation and sulfonylation/semipinacol rearrangements of allylic alcohols were developed using cheap and stable RSO2Na (R = CF3, Ph) as reagents. Various β-trifluoromethyl and sulfonated ketones were obtained in moderate to excellent yields. This strategy provides a facile, direct, and complementary approach to construct all-carbon quaternary stereocenters. In addition, the reaction has the advantages of being chemical oxidant-free and metal-free and has safe and mild reaction conditions.
Metal-Free Transfer Hydrobromination of C-C Triple Bonds
Chen, Weiqiang,Oestreich, Martin
supporting information, p. 4531 - 4534 (2019/06/27)
A transfer hydrobromination of C-C triple bonds inititated by Br?nsted acids is reported. Hydrogen bromide is released stepwise from a bench-stable cyclohexa-1,4-diene-based surrogate, generating biphenyl and ethylene as waste. A range of vinyl bromides was prepared from terminal and internal, mainly acceptor-substituted alkynes with good functional-group tolerance.
A catalytic allylic cation-induced intermolecular allylation-semipinacol rearrangement
Xu, Ming-Hui,Dai, Kun-Long,Tu, Yong-Qiang,Zhang, Xiao-Ming,Zhang, Fu-Min,Wang, Shao-Hua
supporting information, p. 7685 - 7688 (2018/07/15)
A catalytic intermolecular semipinacol rearrangement induced by allylic carbocations has been realized. This tandem reaction is highly efficient under the catalysis of ZnBr2, generating a wide range of α-homoallyl substituted ketones which contain all-carbon quaternary centres in good to excellent yields (up to 98%) with moderate to high diastereoselectivities (up to >20?:?1). Synthetic application of this novel methodology in the construction of core structures of natural products is also reported.