Richard F. Heck

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Richard F. Heck
Heck in 2010
Born
Richard Frederick Heck

(1931-08-15)August 15, 1931
Springfield, Massachusetts, U.S.
DiedOctober 9, 2015(2015-10-09) (aged 84)
Manila, Philippines
NationalityAmerican
Alma materUCLA (BS, PhD)
Known forHeck reaction
SpouseSocorro Nardo-Heck (died 2012)
AwardsGlenn T. Seaborg Medal (2011)
Nobel Prize in Chemistry (2010)
Scientific career
FieldsChemistry
InstitutionsUniversity of Delaware
Hercules
ETH Zurich
De La Salle University
ThesisMethoxyl and aryl groups in substitution and rearrangement (1955)
Doctoral advisorSaul Winstein

Richard Frederick Heck (August 15, 1931 – October 9, 2015) was an American chemist noted for the discovery and development of the

organic chemical reactions that couple aryl halides with alkenes. The analgesic naproxen
is an example of a compound that is prepared industrially using the Heck reaction.

For his work in

Akira Suzuki.[1]

Early life and education

Heck was born in

Hercules Corporation in Wilmington, Delaware in 1956, working initially on polymer chemistry.[3]

Career

Akira Suzuki, Ei-ichi Negishi, and Richard Heck, Nobel Prize Laureates 2010, at a press conference at the Royal Swedish Academy of Sciences
in Stockholm.

At Hercules, Heck soon became interested in

arylmercury compounds with olefins using palladium as a catalyst.[3] This work was published in a series of seven consecutive articles in the Journal of the American Chemical Society for which Heck was the sole author.[6]

During the early 1970s, Tsutomu Mizoroki independently reported the use of the less toxic aryl halides as the coupling partner in the reaction.[7][8] Heck became a professor of chemistry at the University of Delaware's Department of Chemistry and Biochemistry in 1971, where he continued to improve the transformation, developing it into a powerful synthetic method for organic synthesis.[3]

The importance of this reaction grew as it was taken up by others in the organic synthesis community.[9][10] In 1982, Heck was able to write an Organic Reactions chapter that covered all the known instances in just 45 pages.[11] By 2002, applications had grown to the extent that the Organic Reactions chapter published that year, limited to intramolecular Heck reactions, covered 377 pages. These reactions, a small part of the total, couple two parts of the same molecule.[12] The reaction is now one of the most widely used methods for the creation of

carbon-carbon bonds in the synthesis of organic chemicals. It has been subject to numerous scientific review articles, including a monograph dedicated to this subject published in 2009.[13]

Heck's contributions were not limited to the activation of halides by the oxidative addition of palladium. He was the first to fully characterize a π-allyl metal complex,[4] and the first to elucidate the mechanism of alkene hydroformylation.[5]

Palladium-catalyzed coupling reactions

See also:
Palladium-catalyzed coupling reactions

Heck's work set the stage for a variety of other

pharmaceutical drugs such as naproxen.[15]

Of the several reactions developed by Heck, the greatest societal impact has been from the palladium-catalyzed coupling of an alkyne with an aryl halide. This is the reaction that was used to couple fluorescent dyes to DNA bases, allowing the automation of DNA sequencing and the examination of the human genome; the reaction also allows biologically important proteins to be tracked.[16][17] In Sonogashira's original report of what is now known as the Sonogashira coupling, his group modified an alkyne coupling procedure previously reported by Heck, by adding a copper(I) salt.[18]

Later life and death

Heck retired from the University of Delaware in 1989, where he became the Willis F. Harrington Professor Emeritus in the Department of Chemistry and Biochemistry. Its annual lectureship was named in his honor in 2004. In 2005, he was awarded the

Akira Suzuki "for palladium-catalyzed cross couplings in organic synthesis".[1][21][22] In 2011, Heck was awarded the Glenn T. Seaborg Medal for this work. In 2012, he was appointed by De La Salle University in Manila as an adjunct professor in its chemistry department. He had moved to Quezon City, Philippines after retirement, with his wife, Socorro Nardo-Heck. The couple had no children.[23][24]

Heck died on October 9, 2015, in Manila in a public hospital. His wife predeceased him by 2 years.[25][26]

Honorary degrees

Heck received honorary doctorates from the Faculty of Pharmacy at Uppsala University in 2011[27] and De La Salle University in 2012.[28]

See also

References

  1. ^ a b Press release 6 October 2010, Royal Swedish Academy of Sciences, retrieved October 6, 2010
  2. Boston Globe
    .
  3. ^
    doi:10.1016/S0022-328X(98)01136-X
    .
  4. ^
    doi:10.1021/ja01488a067
    .
  5. ^
    doi:10.1021/ja01480a017
    .
  6. doi:10.1021/ja01022a034
    . and six further articles, pages 5526–5548
  7. doi:10.1246/bcsj.44.581
    .
  8. doi:10.1021/jo00979a024
    .
  9. PMID 11749313
    .
  10. PMID 21677934
    .
  11. ISBN 0471264180
    .
  12. ISBN 0471264180
    .
  13. OCLC 233173519
    .
  14. PMID 22573393
    .
  15. doi:10.1021/op960009e
    .
  16. S2CID 46474691
    .
  17. PMID 25025771
    .
  18. doi:10.1016/S0040-4039(00)91094-3
    .
  19. ^ "Richard Heck, professor emeritus and Nobel laureate, dies". udel.edu. October 10, 2015. Retrieved August 22, 2022.
  20. ^ "2006 ACS National Award Winners". C&EN. 84 (6): 34–38. February 6, 2006. Archived from the original on August 6, 2007..
  21. ^ "Richard F. Heck – Interview". Nobelprize.org. October 7, 2010. Archived from the original on October 14, 2010. Retrieved October 7, 2010.
  22. ^ "BBC News – Molecule building work wins Nobel". bbc.co.uk. October 6, 2010. Archived from the original on October 7, 2010. Retrieved October 6, 2010.
  23. ^ Suarez, Larissa Mae (October 7, 2010). "US scientist residing in Philippines wins 2010 chemistry Nobel". GMANews.tv.
  24. ^ Quismundo, Tarra. "He's the only Nobel winner living in RP". Inquirer.net. Archived from the original on October 10, 2010.
  25. New York Times
    . Retrieved October 16, 2015.
  26. ^ Francisco, Rosemarie (October 10, 2015). "Nobel laureate chemist Richard Heck, 84, dies in Manila". Reuters. Archived from the original on March 5, 2016. Retrieved August 22, 2022.
  27. ^ "Honorary Doctors of the Faculty of Pharmacy". uu.se. Retrieved May 28, 2018.
  28. ^ "Make Life Simple" Through Chemistry, Nobel Laureate Dr. Richard Heck's Goal"". nast.ph. Retrieved May 28, 2018.

External links

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