title: Diverse sp(3) C-H functionalization through alcohol β-sulfonyloxylation.
abstract: Site-selective C-H functionalization has emerged as an attractive tool for derivatizing complex synthetic intermediates, but its use for late-stage diversification is limited by the functional groups that can be introduced, especially at unactivated sp(3)-hybridized positions. To overcome this, we introduce a strategy that directly installs a sulfonyloxy group at a β-C-H bond of a masked alcohol and subsequently employs nucleophilic substitution reactions to prepare various derivatives. Hydroxyl groups are widely found in bioactive molecules and are thus readily available as synthetic handles. A directing group is easily added (and subsequently removed) from the alcohols such that a formal site-selective β-C-H sulfonyloxylation of these alcohols is achieved. Substitution reactions with carbon, nitrogen, oxygen and other nucleophiles then lead to diverse functionalizations that may help to streamline the synthesis of complex analogues for drug discovery.
authors.affiliation: Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, USA.
authors.forename: Yan
authors.initials: Y
authors.lastname: Xu
authors.affiliation: Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, USA.|Department of Chemistry, Lishui University, Lishui City 323000, People's Republic of China.
authors.forename: Guobing
authors.initials: G
authors.lastname: Yan
authors.affiliation: Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, USA.
authors.forename: Zhi
authors.initials: Z
authors.lastname: Ren
authors.affiliation: Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, USA.
authors.forename: Guangbin
authors.initials: G
authors.lastname: Dong
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry*
chemical_list: D000438:Alcohols; D013450:Sulfones