文献类型：期刊文献

英文题名：Solvent-Switched Benzylic Methylene Functionalization: Addition, Ring-Opening, Cyclization, and Unexpected Cleavage of C-O and C-C Bonds

作者：Li, Deng Yuan;Shang, Xue Song;Chen, Guo Rong;Liu, Pei Nian[1]

机构：[1]E China Univ Sci & Technol, Shanghai Key Lab Funct Mat Chem, Shanghai 200237, Peoples R China; E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

年份：2013

卷号：15

期号：15

起止页码：3848

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000322853000012)，CCR-EXPANDED(收录号:WOS:000322853000012)】；

基金：This work was supported by the National Natural Science Foundation of China (Project Nos. 21172069 and 21190033), the Innovation Program of Shanghai Municipal Education Commission (Project No. 12ZZ050), the Basic Research Program of the Shanghai Committee of Science and Technology (Project No. 13NM1400802), and the Fundamental Research Funds for the Central Universities.

语种：英文

摘要：Intermolecular benzylic methylene functionalization of exo-cyclic enol ethers has been achieved using imines as reagents and potassium tertbutoxide as the catalyst. Depending on the solvent used, the reaction proceeds by two pathways. In THF, an addition/elimination reaction of exo-cyclic enol ethers with imines provides dihydroisobenzofuran derivatives in good yield. In DMSO, an addition/ring-opening/cyclization cascade reaction occurs with unexpected cleavage of C-O and C-C bonds, affording isoquinolin-1(2H)-one products in high yield under ambient reaction conditions.