title: Synthesis of Lactones via C-H Functionalization of Nonactivated C(sp3)-H Bonds.
abstract: An electron-deficient amide is utilized as a directing group to functionalize nonactivated C(sp3)-H bonds through radical 1,5-hydrogen abstraction. The γ-bromoamides formed are subsequently converted to γ-lactones under mild conditions. The method described is not limited to tertiary and secondary positions but also allows functionalization of primary nonactivated sp3-hybridized positions in a one-pot sequence. In addition, the broad functional group tolerance renders this method suitable for the late-stage introduction of γ-lactones into complex carbon frameworks.
authors.affiliation: Department of Chemistry, Technical University of Munich , Lichtenbergstraße 4, 85747 Garching, Germany.
authors.forename: Johannes
authors.initials: J
authors.lastname: Richers
authors.affiliation: Department of Chemistry, University of Basel , St. Johanns-Ring 19, 4056 Basel, Switzerland.
authors.forename: Michael
authors.initials: M
authors.lastname: Heilmann
authors.affiliation: Department of Chemistry, Technical University of Munich , Lichtenbergstraße 4, 85747 Garching, Germany.
authors.forename: Markus
authors.initials: M
authors.lastname: Drees
authors.affiliation: Department of Chemistry, University of Basel , St. Johanns-Ring 19, 4056 Basel, Switzerland.|Department of Biosystems Science and Engineering, ETH Zurich , Mattenstrasse 26, 4058 Basel, Switzerland.
authors.forename: Konrad
authors.identifier: 0000-0002-3351-6121
authors.initials: K
authors.lastname: Tiefenbacher