Electrochemically Driven Hydrogen Atom Transfer Catalysis: A Tool for C(sp3)/Si-H Functionalization and
Sheng Zhang1, Michael Findlater2
1Institutes of Physical Science and Information Technology, Key Laboratory of Structure and Functional Regulation of Hybrid Materials of Ministry of Education, Anhui University, Hefei, Anhui 230601, China.
Abstract:
Electrochemically driven hydrogen atom transfer (HAT) catalysis provides a complementary approach for the transformation of redox-inactive substrates that would be inaccessible to conventional electron transfer (ET) catalysis. Moreover, electrochemically driven HAT catalysis could promote organic transformations with either hydrogen atom abstraction or donation as the key step. It provides a versatile and effective tool for the direct functionalization of C(sp3)-H/Si-H bonds and the hydrofunctionalization of alkenes. Despite these attractive properties, electrochemically driven HAT catalysis has been largely overlooked due to the lack of understanding of both the catalytic mechanism and how catalyst selection should occur. In this Review, we give an overview of the HAT catalysis applications in the direct C(sp3)-H/Si-H functionalization and hydrofunctionalization of alkenes. The mechanistic pathways, physical properties of the HAT mediators, and state-of-the-art examples are described and discussed.
More Related Videos
12:08Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
Published on: June 24, 2022
08:40Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production
Published on: December 6, 2021
Related Concept Videos
Reduction of Alkenes: Catalytic Hydrogenation
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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: 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...
Electrophilic Addition to Alkynes: Hydrohalogenation
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
