title: Ring Expansion via Cleavage of Benzylic C-C Bonds Enabling Direct Synthesis of Medium Ring-Fused Benzocarbocycles.
abstract: A fluoride-anion-induced, regioselective ring expansion of benzocyclic ketones and α-aryl cycloketones has been developed via insertion of arynes into unactivated benzylic C-C bonds. This reaction provides a straightforward, transition-metal-free avenue to prepare medium ring-fused benzocarbocycles by creating "noble" seven-, eight-, and nine-membered rings. Applications of this method in the creation of medium-sized exocyclic and inner benzocyclic olefins, nine-membered lactones, and lactams are described.
authors.affiliation: Center for Organic Chemistry, Frontier Institute of Science and Technology, Xi'an Jiaotong University, Xi'an, Shaanxi, 710054, P. R. China.
authors.forename: Bin
authors.initials: B
authors.lastname: Rao
authors.affiliation: Center for Organic Chemistry, Frontier Institute of Science and Technology, Xi'an Jiaotong University, Xi'an, Shaanxi, 710054, P. R. China.
authors.forename: Jinghua
authors.initials: J
authors.lastname: Tang
authors.affiliation: Center for Organic Chemistry, Frontier Institute of Science and Technology, Xi'an Jiaotong University, Xi'an, Shaanxi, 710054, P. R. China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Wei
authors.affiliation: Center for Organic Chemistry, Frontier Institute of Science and Technology, Xi'an Jiaotong University, Xi'an, Shaanxi, 710054, P. R. China. zengxiaoming@mail.xjtu.edu.cn.
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Zeng
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000475:Alkenes; D001593:Benzyl Compounds; D007659:Ketones
keywords: C−C bond cleavage; arynes; medium-sized carbocycles; ring expansion; synthetic methods