New! Sign up for our free email newsletter.
Science News
from research organizations

From C-H to C-C at room temperature

Date:
December 27, 2017
Source:
Institute for Basic Science
Summary:
By oxidizing the iridium center of the reaction intermediate, scientists achieve arylation of C-H bonds at mild conditions.
Share:
FULL STORY

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.


Story Source:

Materials provided by Institute for Basic Science. Note: Content may be edited for style and length.


Journal Reference:

  1. Kwangmin Shin, Yoonsu Park, Mu-Hyun Baik, Sukbok Chang. Iridium-catalysed arylation of C–H bonds enabled by oxidatively induced reductive elimination. Nature Chemistry, 2017; DOI: 10.1038/nchem.2900

Cite This Page:

Institute for Basic Science. "From C-H to C-C at room temperature." ScienceDaily. ScienceDaily, 27 December 2017. <www.sciencedaily.com/releases/2017/12/171227100048.htm>.
Institute for Basic Science. (2017, December 27). From C-H to C-C at room temperature. ScienceDaily. Retrieved March 28, 2024 from www.sciencedaily.com/releases/2017/12/171227100048.htm
Institute for Basic Science. "From C-H to C-C at room temperature." ScienceDaily. www.sciencedaily.com/releases/2017/12/171227100048.htm (accessed March 28, 2024).

Explore More

from ScienceDaily

RELATED STORIES