title: Terminal-Selective Functionalization of Alkyl Chains by Regioconvergent Cross-Coupling.
abstract: Hydrocarbons are still the most important precursors of functionalized organic molecules, which has stirred interest in the discovery of new C-H bond functionalization methods. We describe herein a new step-economical approach that enables C-C bonds to be constructed at the terminal position of linear alkanes. First, we show that secondary alkyl bromides can undergo in situ conversion into alkyl zinc bromides and regioconvergent Negishi coupling with aryl or alkenyl triflates. The use of a suitable phosphine ligand favoring Pd migration enabled the selective formation of the linear cross-coupling product. Subsequently, mixtures of secondary alkyl bromides were prepared from linear alkanes by standard bromination, and regioconvergent cross-coupling then provided access to the corresponding linear arylation product in only two steps.
authors: University of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-, 4056, Basel, Switzerland.
authors: Stéphanie
authors: S
authors: Dupuy
authors: University of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-, 4056, Basel, Switzerland.
authors: Ke-Feng
authors: KF
authors: Zhang
authors: University of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-, 4056, Basel, Switzerland.
authors: Anne-Sophie
authors: AS
authors: Goutierre
authors: University of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-, 4056, Basel, Switzerland.
authors: Olivier
authors: 0000-0002-0847-8493
authors: O
authors: Baudoin
keywords: C−C coupling; alkyl bromides; homogeneous catalysis; palladium; remote functionalization