HECK, RICHARD F. / Chimie / Chercheurs

Centre International de Recherche Scientifique





Willis F. Harrington Professor Emeritus, Organic chemistry, at the University of Delaware, Department of Chemistry and Biochemistry, USA.

Thèmes de recherche

During the late 1960\'s Heck discovered that arylmercury compounds undergo coupling reactions with alkenes when treated with either stoichiometric or catalytic palladium reagents. In the early 1970\'s, Heck (independently with Mizoroki) reported that these reactions could also carried out using less toxic aryl halides in place of the mercury reagents, giving rise to the modern form of the reaction. This transformation has become known as the Heck Reaction, in honor of Heck\'s central contributions to its development.

Over the ensuing years, the Heck Reaction has become one of the most widely practiced transformations for carbon-carbon bond formation in organic synthesis, having generated over 5600 publications relating to the \"Heck Reaction\". The Heck Reaction has had broad impact. The transformation has been used to prepare countless complex organic molecules, including many pharmaceutical agents. A modification of the Heck Reaction, know as the Sonogashira Coupling, plays a key role in preparing the fluorescent dyes used in DNA sequencing. The Heck Reaction has been subject of numerous review articles, including a recent monograph dedicated entirely to the transformation.

In addition to the development of Heck Reaction, Richard Heck\'s work laid the foundation for much modern organometallic cross-coupling chemistry, including the reactions of aryl halides with boron reagents (Suzuki-Miyaura coupling), organotin reagents (Stille coupling), organomagnesium compounds (Kumada-Corriu coupling), silanes (Hiyama coupling) and organozincs reagents (Negishi coupling), as well as with alcohols and amines (Buchwald-Hartwig coupling). In addition, Heck was the first to characterize a palladium pi-allyl complex, contributing to the development of the Tsuji-Trost Reaction, and was the first to correctly propose the mechanism for alkene formylation. In addition, the Heck group also developed the palladium-catalyzed carbonylation of aryl halides, a widely used method for the preparation of carboxylate derivatives.

Prix et récompenses

2010 Nobel Prize in Chemistry, alongside fellow researchers Akira Suzuki, of Hokkaido University in Sapporo, Japan, and Ei-Ichi Negishi, of Purdue University, “for palladium-catalyzed cross couplings in organic synthesis.”

His contributions have previously been recognized by the Wallace H. Carothers Award, bestowed by the Delaware section of the American Chemical Society in 2005, and the American Chemical Society Award for Creative Research in Synthetic Methods, in 2006.

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