1979 Nobel Prize in Chemistry
Reason for Award
for the development of the use of boron- and phosphorus-containing compounds into important reagents in organic synthesis (development of new methods in organic synthesis)
Laureates
United States of America
West Germany
Explanation
The medicines and plastics we use every day are made through a chemical “cooking” called organic synthesis. In 1979, Mr. Brown and Mr. Wittig received the Nobel Chemistry Prize because they invented indispensable “seasonings” for that cooking. Mr. Brown created reagents based on boron, and Mr. Wittig created reagents based on phosphorus; these make reactions go faster and more cleanly. Their tools allow chemists to build molecules in the exact shapes they need, leading to new drugs and materials. It is like giving origami artists special rulers and patterns so even hard models can be folded easily. Their ideas have become everyday basic tools used by chemists all over the world.
Related Keywords
hydroboration
Hydroboration is the addition of BH3 or substituted boranes across carbon–carbon multiple bonds, a reaction systematised by Brown. The addition is syn and places boron on the terminal carbon, giving anti-Markovnikov products. A simple oxidation furnishes alcohols, whereas halogenolysis provides halides, allowing many functional groups to be installed in one pot. By tuning ligands and borane frameworks, the reaction has been extended to catalytic versions with exquisite stereo- and regio-control. It now serves as a key entry to boronic esters that participate in cross-coupling reactions.
Wittig reaction
The Wittig reaction forms carbon–carbon double bonds by condensing an aldehyde or ketone with a phosphonium ylide, passing through an oxaphosphetane intermediate. Formation of a strong P=O bond drives the reaction, affording high yields and selectivity. E/Z stereochemistry depends on whether the ylide is stabilised or unstabilised and can be tuned by changing reaction conditions. Variants such as Still–Gennari and Horner–Wadsworth–Emmons use modified reagents to access a wider spectrum of olefin geometries. The reaction is often used in late stages of drug and natural product syntheses, shortening synthetic routes.
borane reagent
Boranes are BH3 or its derivatives that act as Lewis acids yet serve as hydride donors in hydroboration and reduction reactions. Species such as BH3·THF, 9-BBN, and catecholborane each differ in reactivity and selectivity. Via alkylborane intermediates, multistep functional-group interconversions can be achieved, and the products are valuable precursors for cross-coupling. The vacant p-orbital facilitates π-complex formation and electrophilic addition to unsaturated bonds. For safety, solid-supported and “protected” boranes have been developed, broadening their industrial use.
phosphonium ylide
Phosphonium ylides are λ^5-phosphoranes obtained by deprotonating a quaternary phosphonium salt, bearing a negatively charged carbon adjacent to a positively charged phosphorus. Their high nucleophilicity enables reaction with carbonyl compounds, driven by the formation of a strong P=O bond. Stabilised (electron-withdrawing) and unstabilised ylides differ dramatically in reactivity and in the stereochemistry of the resulting alkene. Some ylides are chromophoric and have been utilised in photochemical reactions and spectroscopic analyses. Readily available phosphonium salts are now commercially supplied, allowing use from laboratory to plant scale.
functional group interconversion
Functional-group interconversion (FGI) is the transformation of one functional group in a molecule into another, enabling flexible synthetic design. An archetypal example is oxidation of an alkylborane obtained via hydroboration to give an alcohol, as pioneered by Brown. The Wittig reaction converts a carbonyl group into an alkene in a single step, highly valuable in late-stage synthesis. The quality of an FGI is judged not only by yield but by selectivity, mildness, and environmental impact. Recently, catalytic one-pot processes have emerged, attracting attention from the viewpoint of green chemistry.
stereochemistry
Stereochemistry deals with the three-dimensional arrangement of atoms in molecules and directly influences drug activity and material properties. Hydroboration provides syn addition, introducing groups on the same side of a double bond and thus offers high stereoselectivity. In the Wittig reaction, the E/Z ratio can be controlled by the ylide’s nature, an essential feature for synthesising complex natural products. Concepts of stereochemical control inform the design of organocatalysts, asymmetric metal catalysts, and more recently artificial enzymes. Precise stereocontrol not only affects drug efficacy but also reduces side effects and improves material performance.
green chemistry
Green chemistry is a design philosophy aiming to minimize environmental impact, focusing on waste reduction, toxicity avoidance, and energy efficiency. Hydroboration and the Wittig reaction, with their high yields and selectivities, align with green chemistry principles by limiting by-products. Recent research introduces aqueous media and catalytic adaptations to further reduce environmental burden. The 12 principles of green chemistry encourage reagent choice and pathway shortening at the planning stage. Widespread adoption of such environmentally benign reactions is essential for achieving a sustainable society.