Related Experiment Video
Updated: May 15, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Rhodium-catalyzed intramolecular silylation of unactivated C(sp3)-H bonds
Yoichiro Kuninobu1, Takahiro Nakahara, Hirotaka Takeshima
1Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Okayama 700-8530, Japan. kuninobu@mol.f.u-tokyo.ac.jp
Abstract:
The treatment of a variety of hydrosilanes, each incorporating a benzylic C(sp(3))-H bond, with a rhodium catalyst resulted in intramolecular dehydrogenative silylation. This silylation reaction was found to occur at typically unreactive C(sp(3))-H bonds located at terminal positions on alkyl chains. Interestingly, the rhodium catalyst also promoted regioselective silylation at a site internal to an alkyl chain.
Related Concept Videos
Preparation and Reactions of Sulfides
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
Radical Reactivity: Intramolecular vs Intermolecular
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Radical Substitution: Allylic Bromination
Preparation and Reactions of Thiols
