Related Experiment Video
Updated: Jan 20, 2026
Palladium-Catalyzed Cross Coupling; Heck Coupling Reaction
Published on: April 30, 2023
Regioselective Alkylative Cross-Coupling of Remote Unactivated C(sp3)-H Bonds
Scott M Thullen1, Sean M Treacy1, Tomislav Rovis1
1Department of Chemistry , Columbia University , New York , New York 10027 , United States.
Abstract:
The functionalization of unactivated C(sp3)-H bonds poses a significant challenge due to their ubiquity and relative similarity in most organic frameworks. Herein, we describe the use of a combined photoredox and nickel catalytic system for the regioselective C(sp3)-C(sp3) coupling of unactivated C(sp3)-H bonds and alkyl bromides. Positional selectivity is dictated by a 1,5-hydrogen atom transfer (HAT) reaction by a pendent amide. Interception of this radical by a Ni catalyst allows distal alkylation to occur in good yield and excellent selectivity.
Related Concept Videos
Palladium-Catalyzed Cross Coupling
This experiment will demonstrate the concept of a palladium-catalyzed cross coupling. The set-up of a typical Pd-catalyzed cross coupling reaction will be illustrated. Pd-catalyzed cross coupling reactions have had a profound effect on how synthetic chemists create molecules. These reactions have enabled chemists to construct bonds in new and more efficient ways. Such reactions have found widespread...
Spin–Spin Coupling: One-Bond Coupling
Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)
The central atom need not be NMR-active because its electrons are affected by the electron polarization of the spin-active atoms. However, spin information is transmitted less effectively than in one-bond coupling, and 2J values are usually weaker than 1J values. The energy of...
Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)
The extent of coupling depends on the C‑C bond length, the two H‑C‑C angles, any electron-withdrawing substituents, and the dihedral angle between the involved orbitals. The...
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Bond Energies and Bond Lengths
