Carbon Bond Formations Win 2010 Nobel Prize with Award-Winning Research Documented in CAS Databases

Thanks in part to the innovative work of three scientists, organic chemists have sophisticated tools to synthesize novel carbon-carbon bonded structures. On October 6, 2010, Heck, Negishi, and Suzuki were awarded the Nobel Prize in Chemistry by the Royal Swedish Academy of Sciences for "palladium-catalyzed cross couplings in organic synthesis".1

In cross coupling, reactions describe the process of coupling carbon atoms between two different hydrocarbons to form a new product. The 2010 Nobel Prize in Chemistry recognizes the implications of this work and the unifying use of palladium metal catalysts to increase the rate of the reaction. The ability to synthesize sophisticated and complex carbon-based molecules has significant implications in medicine, electronics, and advanced technological materials.

Notable Beginnings

  • A recent American Chemical Society award winner for creative work in organic chemistry2, Ei-ichi Negishi produced a highly efficient coupling reaction in 19773 that has varied applications in pharmaceuticals today.
  • Akira Suzuki worked under 1979 Nobel Prize winner Herbert C. Brown (DOI:10.1039/b507375h)4 before providing a solution to conjugated alkadienes synthesis using complexed-palladium catalysts (DOI:10.1016/S0040-4039(01)95429-2).5
  • Richard F. Heck found a new method of carbon-carbon bond formation using palladium metal in 1968 (DOI:10.1021/ja01022a034).6 A more in-depth reference and Hecks personal story on palladium metal catalysts provides deeper insight into his contributions to organopalladium research (DOI:10.1055/s-2006-951536).7

"Dr. Heck ran his weekly lab meetings with business-like precision, discussing yields, products, and practical applications," recalls a former student of Hecks and current CAS Editorial Operations Scientist, William Fischetti. While Hecks Nobel Prize winning research began in industry, however, during his time in academia he could explore the full range of arylation possibilities moving toward olefins, alkynes, and conjugated polyenes.8 According to Fischetti, "At the time, our goal was to create new tools like designer palladium catalysts for other organic chemists to synthesize new complex compounds."

The CAS databases include more than 12,000 references for Heck, Suzuki, and Negishi coupled reactions.

CAS congratulates the 2010 Nobel Prize winners for their great scientific accomplishments.

Use SciFinder® and STN® to explore more information about palladium catalysts and Nobel prize winning chemistry to be found in the CAS databases.

Contributed by
Kathryn J. Kitzmiller, Ph.D.


References
  1. The Nobel Prize in Chemistry 2010 Press Release. Nobelprize.org. http://nobelprize.org/nobel_prizes/chemistry/laureates/2010/press.html (accessed October 6, 2010).
  2. Heck, R. F. Acylation, Methylation, and Carboxyalkylation of Olefins by Group VIII Metal Derivatives. J Am. Chem. Soc. 1968, 90 (20), 5518-5526.
  3. King, A. O.; Okukado, N; Negishi, E. Highly General Stereo-, Regio-, and Chemo-Selective Synthesis of Terminal and Internal Conjugated Enynes by the Pd-Catalysed Reaction of Alkynylzinc Reagents with Alkenyl Halides. J. Chem. Soc. Chem. Comm. 1977, 19, 683-684.
  4. Suzuki, A. Carbon-Carbon Bonding Made Easy. Chem. Commun. 2005, 38, 4759-4763.
  5. Miyaura, N.; Yamada, K.; Suzuki, A. A New Stereospecific Cross-Coupling by the Palladium Catalyzed Reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl Halides. Tetrahedron Lett. 1979, 36, 3437-3440.
  6. Wilson, E. ACS Award for Creative Work in Synthetic Organic Chemistry. Chem. Eng. News [Online] 2010, 88, http://pubs.acs.org/isubscribe/journals/cen/88/i07/html/8807awards7.html (accessed October 6, 2010).
  7. Heck, R. F. Cobalt and Palladium Reagents in Organic Synthesis: The Beginning. Synlett 2006, 18, 2855-2860.
  8. Fishetti, W.; Mak, T.; Stakem, F.; Gergory, K.; Jinil, R.; Arnold, L.; Heck, R. F. Palladium-Catalyzed Syntheses of Conjugated Polyenes. J Org. Chem. 1983, 47, 948-955.

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