New method dramatically simplifies olefin synthesis

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New method dramatically simplifies olefin synthesis

Post by bejoy »

Chemists at The Scripps Research Institute (TSRI) have discovered a new method that greatly simplifies, and in many cases enables for the first time, the making of a vast range of organic molecules.

The new method, decarboxylative alkenylation, easily turns carboxylic acids, a relatively cheap, abundant and diverse class of compounds, into alkenes (also called olefins), another large family of compounds commonly used for pharmaceuticals and other applications. It thus should facilitate the discovery and development of a great variety of new drugs and other chemical products.

“This method dramatically simplifies the syntheses of olefins; in fact, it has really changed the way I think about making molecules,†said principal investigator Phil Baran, Darlene Shiley professor of chemistry at TSRI.

The method, published in the edition of Nature, essentially supersedes reactions that have been in chemistry textbooks and in widespread industrial and academic use for decades. Chief among these is the Wittig reaction, discovered in 1954, for which Germany’s Georg Wittig was awarded a share of the Nobel Prize for Chemistry in 1979. The Wittig reaction enables the making of many olefins from precursor compounds, and even though it tends to require a many-step process, chemists have continued to rely heavily on it up to the present.

“Organic chemists have endured this burdensome 'analog' process for decades with little complaint,†Baran said. “Now with this new method we’re bringing olefination into the digital era.â€

The new method originated with a breakthrough by Baran and his laboratory that was described a year ago in the Journal of the American Chemical Society. That transformation allowed the building of many complex drug and other molecules starting from carboxylic acids, using inexpensive metal catalysts.

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