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Nobel Prize in Chemistry 2010 to Richard F. Heck, Ei-ichi Negishi and Akira Suzuki



The Nobel Prize in Chemistry  was awarded jointly to Richard F. Heck, Ei-ichi Negishi and Akira Suzuki "for palladium-catalyzed cross couplings in organic synthesis".
Palladium Catalyzed Coupling Reactions
  There are a family of coupling reactions in which a organometallic reagent (typically a Sn, B, Zn or Mg reagent) is treated with an electrophile (usually an iodide, bromide, or triflate) in the presence of a Pd catalyst, to form cross-coupled products. These reactions are of such importance that each of the organometallic reagent couplings is a separate name reaction, organostannane couplings are Stille reactions, organoborane couplings are Suzuki reactions, organozinc couplings are Negishi reactions, and organomagnesium couplings are Kumada reactions.

    Mechanism: All of these reactions proceed by a common mechanism. The process is initiated by reaction of the Pd(0) species with the halide to form a Pd(II) alkyl iodide (Pd(0) should be considered a nucleophile, and a reducing reagent, much in the way Mg° is in the formation of a Grignard reagent). After this oxidative addition the Pd(II) species (which is now a Pd electrophile) performs a transmetalation on the organometallic component -- a Pd/Sn, Pd/B or Pd/Zn exchange -- to form a diorganopalladium (II) intermediate. This species then undergoes a reductive elimination to form the C-C bond, and return the catalyst to the Pd(0) oxidation state. If a Pd-catalyzed cross-coupling is performed under a CO atmosphere then there may be a C=O insertion, such that both fragments become substituents on a ketone (carbonylative coupling).
     Each of the metals has advantages and disadvantages in their use.
  Stille couplings (Pd/Sn) work well, and organotin compounds are the only organometallic coupling partners that can be purified easily, and they can be stored. However organotin compounds are toxic, and the separation of products from starting materials and byproducts can be very difficult. They are also poorly suited for alkyl couplings, since there are typically several alkyl group on tin. In fact, alkyl couplings are generally problematic, because of potential β-hydride eliminations in either of the two Pd(II) intermediates.
  Suzuki couplings (Pd/B), are usually done using R'-B(OR)2 compounds but they work well even with trialkyl boranes. The alkenyl and alkyl borate starting materials can often be easily made by hydroboration reactions. However, they do require the presence of base to form the boron ate complexes, and organoboranes are too reactive for easy purification. However, left-over starting organoborates, and other byproducts can often be easily removed because of their polar nature.
  Negishi couplings (Pd/Zn) show excellent reactivity, but the organozinc compounds show less functional group compatibility because of their higher reactivity, and the higher reactivity of the Li and Mg reagents often used to prepare them. They seem to be especially well suited for alkyl couplings
Richard F. Heck
Richard F. Heck was born in born August 15, 1931 in Springfield, Massachusetts He earned both his bachelor's degree (1952) and his doctor of philosophy degree (1954) at the University of California, Los Angeles (UCLA)
 In 1971, American chemist Richard F. Heck discovered a previously unknown carbon-carbon bond-forming reaction mediated by palladium, which forms substituted olefins. In his report for the Journal of the American Chemistry Society, Heck wrote that "in spite of some limitations, the organic halide olefinic substitution reaction should prove to be a useful synthetic reaction", which is something of an understatement. Now called the Heck reaction (or the Heck-Mizoroki reaction, for Tsutomu Mizoroki, who detailed a related reaction independently), this process set the framework for countless refinements and extensions to the catalytic organometallic bond forming processes for organic synthesis.

Heck pioneered his field of study virtually alone, with seven sole-author papers in the 1960s, one of which inspired Mizoroki's experiment. He was the first chemist to explain the co-catalyzed hydroformylation reaction, the mechanism which drives all catalytic organometallic reactions. He later taught at the University of Delaware, but retired with some frustration in 1989 when his funding was canceled and he was unable to obtain corporate or government grants to further his research. In retirement he was once quoted as saying, "I'm not doing any chemistry anymore, but I think I've done my share".
books by Richard F. Heck
Organotransition Metal Chemistry: A Mechanistic Approach (1974)
Palladium Reagents in Organic Syntheses (1985)
   
Ei-ichi Negishi  

Ei-ichi Negishi  "pronounced: Ei-ichi (Â-E-chE) Negishi (Na-gE-shE)" was Born in 1935, Negishi came to the United States in 1960 after graduating from the University of Tokyo.
     In 1962, while studying for his doctorate at the University of Pennsylvania, he met Purdue chemistry professor Herbert C. Brown—a pioneer in synthetic organic chemistry. Negishi admired Brown’s research and predicted,
“Brown will change the whole world of organic chemistry and that is why I came to Purdue.” With Brown as a mentor, Negishi arrived in West Lafayette as a postdoctoral researcher in 1966.
     He then moved to Syracuse University where he served as an assistant professor (1972-76) and associate professor (1976-79). 

     Dr. Negishi joined the faculty at Purdue in 1979—the same year Brown was awarded the Nobel Prize in Chemistry—and has been a researcher in this building for more than thirty years.
Awards

•    Fulbright-Smith-Mund All Expense Scholarship, 1960-63
•    J. S. Guggenheim Memorial Foundation Fellowship, 1987
•    A. R. Day Award, 1996
•    Chemical Society of Japan Award, 1996
•    American Chemical Society Organometallic Chemistry Award, 1998
•    Herbert N. McCoy Award - Purdue University, 1998
•    Alexander von Humboldt Award, Senior Researcher Germany, 1998-2001
•    Herbert C. Brown Distinguished Professor - Purdue University, 1999
•    Sir Edward Frankland Prize Lectureship, 2000
•    Citation of Negishi Cross-Coupling - Merck Index, 13th Ed., 2001
•    Sigma Xi Award - Purdue Univeristy, 2003
•    Gold Medal of Charles University, Prague, Czech Republic, 2007
•    Yamada-Kaga Prize, 2007
•    American Chemical Society Award for Creative Work in Synthetic Organic Chemistry, 2010
•    Nobel Prize in Chemistry, 2010
•    Japanese Person of Cultural Merit, 2010
•    Japanese Order of Culture, 2010
•    Sagamore of the Wabash, State of Indiana, 2011
•    Order of the Griffin, Purdue University, 2011
•    American Academy of Arts & Sciences, 2011

Akira Suzuki
 Professor Akira Suzuki was born in Mukawa-cho, Hokkaido on September 12, 1930. After completing a Ph.D. course in the Graduate School of Science at Hokkaido University in 1959, he became an assistant professor at the Department of Chemical Process Engineering, Faculty of Engineering in 1961. Later, in 1973, he became a professor at the Department of Applied Chemistry. Upon reaching mandatory retirement age in 1994, he became an Emeritus 
Professor at Hokkaido University. He served as a professor at Okayama University of Science in 1994. He also served as a professor at Kurashiki University of Science and the Arts from 1995 until 2002, where he advanced his lifework in research on boron chemistry. His research concerning synthesis and use of an organic boron compound as a doctoral research fellow at H.C. Brown's laboratory (Purdue University, U.S.) for two years from 1963 further advanced this field and achieved many excellent world-leading results after returning to Japan.
 
His work on the cross-coupling reaction of an organic boron compound using palladium as a catalyst, work he reported in 1979, has grown as a field with profound impact on catalytic chemistry and material science, as well as organic synthetic chemistry. Since then he has developed a new research topic globally recognized as the "Suzuki coupling reaction