Nav: Home

Chemists allow boron atoms to migrate

January 17, 2020

Organic molecules with atoms of the semi-metal boron are among the most important building blocks for synthesis products that are needed to produce drugs and agricultural chemicals. However, during the usual chemical reactions used in industry, the valuable boron unit, which can replace another atom in a molecule, is often lost. Chemists at the University of Münster have now succeeded in significantly expanding the range of applications of commercially and industrially used boron compounds, so-called allylboronic esters. The study has been published in the scientific journal "Chem".

Since so-called boronic acid derivatives are very versatile and reliably applicable in their variants, chemists often use them to build up important carbon-carbon couplings (C-C couplings). The most important process using boronic acid derivatives is the Nobel Prize-winning Suzuki-Miyaura coupling. Also widely used in synthesis are the so-called allylboronic esters, which also belong to this class of boron compounds.

In their current study, the chemists headed by Prof. Armido Studer of the Organic Chemical Institute at Münster University are now presenting C-C couplings in which the boron unit from the starting material is retained in the product. The scientists use methods of so-called radical chemistry for this purpose. The principle works like this: The boron unit "migrates" from one carbon atom to the neighbouring atom, thus enabling a second C-C coupling.

Using this method, the chemists can gradually incorporate individual building blocks of molecules at different points in the basic structure. "Since the boron unit remains in the product molecule, i.e. is 'preserved', it can be replaced by another molecular unit, which can be done using the entire spectrum of industrial methods. The commercially available allylboronic esters thus appear in a new guise," says Armido Studer, the lead author of the study. The new method may in future be relevant for the production of drugs. In the future, the new method may be relevant for the production of pharmaceuticals, among other things.
-end-
Original publication:

K. Jana et al. (2020): Radical 1,3-Difunctionalization of Allylboronic Esters with Concomitant 1,2-Boron Shift. Chem; DOI: 10.1016/j.chempr.2019.12.022

University of Münster

Related Molecules Articles:

Water molecules dance in three
An international team of scientists has been able to shed new light on the properties of water at the molecular level.
How molecules self-assemble into superstructures
Most technical functional units are built bit by bit according to a well-designed construction plan.
Breaking down stubborn molecules
Seawater is more than just saltwater. The ocean is a veritable soup of chemicals.
Shaping the rings of molecules
Canadian chemists discover a natural process to control the shape of 'macrocycles,' molecules of large rings of atoms, for use in pharmaceuticals and electronics.
The mysterious movement of water molecules
Water is all around us and essential for life. Nevertheless, research into its behaviour at the atomic level -- above all how it interacts with surfaces -- is thin on the ground.
Spectroscopy: A fine sense for molecules
Scientists at the Laboratory for Attosecond Physics have developed a unique laser technology for the analysis of the molecular composition of biological samples.
Looking at the good vibes of molecules
Label-free dynamic detection of biomolecules is a major challenge in live-cell microscopy.
Colliding molecules and antiparticles
A study by Marcos Barp and Felipe Arretche from Brazil published in EPJ D shows a model of the interaction between positrons and simple molecules that is in good agreement with experimental results.
Discovery of periodic tables for molecules
Scientists at Tokyo Institute of Technology (Tokyo Tech) develop tables similar to the periodic table of elements but for molecules.
New method for imaging biological molecules
Researchers at Karolinska Institutet in Sweden have, together with colleagues from Aalto University in Finland, developed a new method for creating images of molecules in cells or tissue samples.
More Molecules News and Molecules Current Events

Trending Science News

Current Coronavirus (COVID-19) News

Top Science Podcasts

We have hand picked the top science podcasts of 2020.
Now Playing: TED Radio Hour

Our Relationship With Water
We need water to live. But with rising seas and so many lacking clean water – water is in crisis and so are we. This hour, TED speakers explore ideas around restoring our relationship with water. Guests on the show include legal scholar Kelsey Leonard, artist LaToya Ruby Frazier, and community organizer Colette Pichon Battle.
Now Playing: Science for the People

#568 Poker Face Psychology
Anyone who's seen pop culture depictions of poker might think statistics and math is the only way to get ahead. But no, there's psychology too. Author Maria Konnikova took her Ph.D. in psychology to the poker table, and turned out to be good. So good, she went pro in poker, and learned all about her own biases on the way. We're talking about her new book "The Biggest Bluff: How I Learned to Pay Attention, Master Myself, and Win".
Now Playing: Radiolab

Uncounted
First things first: our very own Latif Nasser has an exciting new show on Netflix. He talks to Jad about the hidden forces of the world that connect us all. Then, with an eye on the upcoming election, we take a look back: at two pieces from More Perfect Season 3 about Constitutional amendments that determine who gets to vote. Former Radiolab producer Julia Longoria takes us to Washington, D.C. The capital is at the heart of our democracy, but it's not a state, and it wasn't until the 23rd Amendment that its people got the right to vote for president. But that still left DC without full representation in Congress; D.C. sends a "non-voting delegate" to the House. Julia profiles that delegate, Congresswoman Eleanor Holmes Norton, and her unique approach to fighting for power in a virtually powerless role. Second, Radiolab producer Sarah Qari looks at a current fight to lower the US voting age to 16 that harkens back to the fight for the 26th Amendment in the 1960s. Eighteen-year-olds at the time argued that if they were old enough to be drafted to fight in the War, they were old enough to have a voice in our democracy. But what about today, when even younger Americans are finding themselves at the center of national political debates? Does it mean we should lower the voting age even further? This episode was reported and produced by Julia Longoria and Sarah Qari. Check out Latif Nasser's new Netflix show Connected here. Support Radiolab today at Radiolab.org/donate.