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Herbert C. Brown Award for Creative Research in Synthetic Methods

February 6, 2006 | A version of this story appeared in Volume 84, Issue 6

Credit: Courtesy of Richard Heck
Credit: Courtesy of Richard Heck

Sponsored by the Purdue Borane Research Fund and the Herbert C. Brown Award Endowment

Richard F. Heck, Willis F. Harrington Professor Emeritus at the University of Delaware, is best known for the palladium-mediated coupling of an aryl halide or vinylic halide with an alkene, the reaction that bears his name. The importance of this reaction cannot be overstated. For example, in 1982, Heck's chapter in "Organic Reactions" covered all the known uses of this reaction in 45 pages, but by 2002, applications had grown such that 377 pages were written about the intramolecular Heck reactions alone.

Heck, 74, received a B.S. degree at the University of California, Los Angeles, in 1952. He remained at UCLA and did graduate research with Saul Winstein in the area of neighboring-group participation in the solvolysis of arylsulfonates. After receiving his Ph.D., Heck studied at the Swiss Federal Institute of Technology, Zurich, with Vladimir Prelog. There, he carried out research on the solvolysis of medium-sized cycloalkyl arylsulfonates. He then returned to UCLA and Winstein's group to do more research on neighboring-group effects.

In 1956, Heck joined the staff of Hercules Powder Co., in Wilmington, Del. He started working to form crystalline polymers from polar monomers (vinyl ethers). His study of hydroformylation led to the first proposed mechanism for a transition-metal-catalyzed reaction.

In 1971, he joined the faculty at the University of Delaware, where he continued to study organopalladium chemistry. Of the several reactions that Heck developed there, the coupling of an alkyne with an aryl halide has had a profound impact on science. Its use to couple fluorescent dyes to DNA bases has allowed the automation of DNA sequencing and the elucidation of the human genome. This coupling is called the Sonogashira reaction, a modification of the alkyne-coupling procedure reported by Heck a year earlier. K. Sonogashira's modification was to add a Cu(I) cocatalyst.

Heck's work set the stage for a variety of other Pd-catalyzed couplings, including those with boronic acid derivatives (Suzuki), organotins (Stille), organonickel compounds (Kumada), silanes (Hiyama), and organozincs (Negishi), as well as with alcohols and amines.

Heck's contributions are not limited to the activation of halides by the oxidative addition of Pd(0). Heck was the first to fully characterize a π-allyl metal complex and also the first to elucidate the mechanism of alkene hydroformylation, a reaction that currently is used to produce 15 billion lb of alcohols and aldehydes per year.

Heck retired to Florida in 1989. In 2004, the department of chemistry and biochemistry at the University of Delaware established the Richard F. Heck Lectureship in his honor, and he presented the inaugural lecture.

Heck will present his address before the Division of Organic Chemistry.—Linda Raber



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