title: Solvent-switched benzylic methylene functionalization: addition, ring-opening, cyclization, and unexpected cleavage of C-O and C-C bonds.
abstract: Intermolecular benzylic methylene functionalization of exo-cyclic enol ethers has been achieved using imines as reagents and potassium tert-butoxide 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.
authors.affiliation: Shanghai Key Laboratory of Functional Materials Chemistry and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road 130, Shanghai, China.
authors.forename: Deng Yuan
authors.initials: DY
authors.lastname: Li
authors.forename: Xue Song
authors.initials: XS
authors.lastname: Shang
authors.forename: Guo Rong
authors.initials: GR
authors.lastname: Chen
authors.forename: Pei Nian
authors.initials: PN
authors.lastname: Liu