title: Electrophilic iodine(I) compounds induced semipinacol rearrangement via C-X bond cleavage.
abstract: Neutral electrophilic iodine(I) species proved to be efficient reagents for C-X bond cleavage of various cyclic and acyclic α-silyloxyhalides, and the induced desilylative semipinacol rearrangement provided the corresponding ketones in good yields. The reaction is operationally simple, and proceeds under mild conditions with good functional group compatibility. Mechanistic investigations, including computational studies, were also performed.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University Institution, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan. takemoto@pharm.kyoto-u.ac.jp.
authors.forename: Nobuya
authors.initials: N
authors.lastname: Tsuji
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Kobayashi
authors.forename: Yoshiji
authors.initials: Y
authors.lastname: Takemoto
mesh_terms: D001965:Bromides / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D053138:Cyclohexenes / Q000737:chemistry; D017613:Iodine Compounds / Q000737:chemistry*; D055672:Static Electricity
chemical_list: D001965:Bromides; D002712:Chlorides; D053138:Cyclohexenes; D017613:Iodine Compounds; C519041:semipinacol