Heck, Richard

Heck, R. F. Nolley, J. P., Jr. J. Am. Chem. Soc. 1968, 90, 5518. Richard Heck discovered the Heck reaction when he was an assistant professor at the University of Delaware. Despite having discovered a novel methodology that would see ubiquitous utility in organic chemistry and having published a popular hook," Heck had difficulties in securing funding for his research, he left chemistry and moved to Asia. Now he is retired in Florida. 

Sonogashira K. Tohda, Y. Hagihara, N. Tetrahedron Lett. 1975, 4467. Richard Heck discovered the same transformation using palladium but without the use of copper J. Organomet. Chem. 1975, 93, 259. 

Richard F. Heck The purpose of my paper has been to point out a reaction which appears more widely in the periodic table than most people realize. This general reaction is the insertion reaction and it might be used more widely to make some organometallic compounds which are not available now. 

Van Hecke, Gerald R. Karukstis, Kerry K. Haskell, Richard C McFadden, Catherine S. Wettack, F. Sheldon. J. Chem. Educ. 2002, 79, 837-844. 

Moog, R. S., 268 Mortimer, Robert G., 28 Papanikolas, John M., 194 Scerri, Eric, 59 Schnitker, Jurgen, 207 Schoolcraft, Tracy A., 1 Schwenz, Richard W., 237 Sension, Roseanne J., 220 Spencer, J. N., 268 Tsaparlis, Georgios, 75 Van Hecke, Gerald R., 11 Zielinski, Theresa Julia, 177... 

Richard F. Heck, Palladium Reagents in Organic Synthesis, 1985... 

Over 35 years ago, Richard F. Heck found that olefins can insert into the metal-carbon bond of arylpalladium species generated from organomercury compounds [1], The carbopalladation of olefins, stoichiometric at first, was made catalytic by Tsutomu Mizoroki, who coupled aryl iodides with ethylene under high pressure, in the presence of palladium chloride and sodium carbonate to neutralize the hydroiodic acid formed (Scheme 1) [2], Shortly thereafter, Heck disclosed a more general and practical procedure for this transformation, using palladium acetate as the catalyst and tri-w-butyl amine as the base [3], After investigations on stoichiometric reactions by Fitton et al. [4], it was also Heck who introduced palladium phosphine complexes as catalysts, enabling the decisive extension of the ole-fination reaction to inexpensive aryl bromides [5],... 

Fig. 16.35 (part I). Heck reaction of an aryl triflate with acrylic acid methyl ester under "classical," i.e., the Richard Heck conditions with a mechanistic analysis of the beginning of the reaction sequence, namely the formation of the catalytically active Pd(0) complex (= compound F). 

Richard F. Heck (bom 1931) was a student of Saul Winstein (UCLA) and Vladimir Prelog (ETH Zurich). He started mechanistic work on homogeneous catalysis in 1956 when he entered Hercules Inc. (Wilmington, Del., USA) as a research chemist. He pioneered the elucidation of reaction mechanisms of organometallic processes, e. g., hydro-formylation and Ziegler-Natta polymerization, and published a number of key papers about the chemical and mechanistic backgrounds of these reactions. He was a chemistry professor at the University of Delaware from 1971 until his retirement in 1989. For the Heck reaction the reader is referred to Section 3.1.6. 

Palladium-Catalyzed Vinylation of Organic Halides Richard F. Heck... 

Palladium-catalyzed substitutions of aryl halides have emerged as a powerful tool for making carbon-carbon bonds. The most widely used of these arylations leads to substitution of a vinylic hydrogen of an alkene by an aryl group and is called the Heck reaction after Richard F. Heck (University of Delaware) who pioneered its development. 

Richard F. Heck, Ei-ichi Negishi and Akira Suzuki for palladium-catalysed cross couplings in organic synthesis. 

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