My watch list
my.chemeurope.com  
Login  

From C-H to C-C at room temperature

By oxidizing the iridium center of the reaction intermediate, scientists achieve arylation of C-H bonds at mild conditions

03-Jan-2018

IBS, published in Nature Chemistry

Oxidation of the metal (M, iridium, blue pathway) leads to a 19 kcal/mol decrease in reaction's energy barrier, and allows the arylation to occur at room temperature.

Carbon-carbon (C-C) bonds make up the skeleton of all organic molecules. However, creating such ubiquitous C-C bonds artificially is still a complicated task. In particular, since several molecules used in medicine, pharmacology and material chemistry contain aryl groups, devising a way to efficiently and selectively introduce this chemical group is a major goal for organic chemists. Currently, most arylation reactions require harsh reaction conditions, including high temperatures and excess additives.

Scientists at the Center for Catalytic Hydrocarbon Functionalization, within the Institute for Basic Science (IBS, South Korea), devised a method to selectively introduce aryl groups into C-H bonds at room temperature. Published in Nature Chemistry, the study also clarifies the details of this reaction, which turned out to be different from the conventional idea.

In simple terms, the procedure consists of three main steps. Firstly, the iridium catalyst activates the C-H containing substrate. Secondly, the arylsilane attacks the metal, creating an intermediate molecule. The team crystallized such intermediate and demonstrated that oxidizing the iridium center of the intermediate (third step) is beneficial to achieve a low energy arylation reaction.

The proposed reaction mechanism was verified with electroparamagnetic resonance, cyclic voltametry and computer simulations. "Developing more efficient and environmetally benign oxidation system is our next goal," concludes Kwangmin Shin, first author of the study.

Facts, background information, dossiers
  • Arylation
  • chemical reactions
More about Institute for Basic Science
  • News

    Naked molecules dancing in liquid become visible

    Moving, vibrating and leaping molecules make up our world. However, capturing their movement is not an easy task. IBS scientists at the Center for Soft and Living Matter, within the Institute for Basic Science (IBS), were able to see the movement of molecules stored inside a graphene pocket ... more

    Large single-crystal graphene is possible!

    Boasting the conductivity, strength and flexibility we wished for, graphene was proposed as one of the most likely substitutes for silicon and other materials. Its launch into the market however is still slow. What is curbing graphene from industrial applications? One factor is that top qua ... more

    Explaining how 2-D materials break at the atomic level

    Cracks sank the 'unsinkable' Titanic; decrease the performance of touchscreens and erode teeth. We are familiar with cracks in big or small three-dimensional (3D) objects, but how do thin two-dimensional (2D) materials crack? 2D materials, like molybdenum disulfide (MoS2), have emerged as a ... more

  • Videos

    Multiresponsive nanosurfactant integrates functions of molecular surfactants

    (0:00) Droplets coated with nanosurfactants are hit with a laser which clumps the droplets into a two-dimensional hexagonal structure and rotates them much like gears. (0:17) Droplets are randomly distributed and then a laser is turned on which attracts them together into a bilayer aggregat ... more

Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE