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Richard F. Heck

April 08, 2024

Richard Frederick Heck (August 15, 1931 – October 9, 2015) was an American chemist noted for the discovery and development of the Heck reaction, which uses palladium to catalyze 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.

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
Doctoral advisorSaul Winstein

For his work in palladium-catalyzed coupling reactions and organic synthesis, Heck was awarded the 2010 Nobel Prize in Chemistry, shared with the Japanese chemists Ei-ichi Negishi and Akira Suzuki.[1]

Early life and education edit

Heck was born in Springfield, Massachusetts in 1931.[2] He moved to Los Angeles when eight years old and later attended the University of California, Los Angeles (UCLA), gaining a bachelor's degree in 1952 and then a Ph.D. in 1954 working under the supervision of Saul Winstein on the chemistry of aryl sulfonates. After postdoctoral research at the ETH in Zurich, Switzerland with Vladimir Prelog, and then back at UCLA, Heck took a position with the Hercules Corporation in Wilmington, Delaware in 1956, working initially on polymer chemistry.[3]

Career edit

 
Peter Diamond, Dale T. Mortensen, Christopher A. Pissarides, Konstantin Novoselov, Andre Geim, 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 organometallic chemistry, including work with David S. Breslow on organocobalt reactions.[4][5] This led to the development of the Heck reaction, which began with his investigation during the late 1960s of the coupling of 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 edit

See also: Palladium-catalyzed coupling reactions

Heck's work set the stage for a variety of other palladium-catalyzed coupling reactions, including those of aryl halides with derivatives of boronic acid (Suzuki–Miyaura coupling), organotin reagents (Stille coupling), organomagnesium compounds (Kumada-Corriu coupling), silanes (Hiyama coupling), and organozincs (Negishi coupling), as well as with amines (Buchwald–Hartwig amination) and alcohols.[14] These palladium-catalyzed coupling reactions are now widely practiced in organic synthesis, including for the manufacture of 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 edit

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 Wallace H. Carothers Award, which recognizes creative applications of chemistry that have had substantial commercial impact. He was awarded the 2006 Herbert C. Brown Award for creative research in synthetic methods.[19][20] On October 6, 2010, the Swedish Royal Academy of Sciences awarded Heck the Nobel Prize in Chemistry, which he shared with Ei-ichi Negishi and 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 edit

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 edit

References edit

  1. ^ a b Press release 6 October 2010, Royal Swedish Academy of Sciences, retrieved October 6, 2010
  2. ^ Finucane, Martin (October 6, 2010). "Nobel Prize winner is Springfield native". Boston Globe.
  3. ^ a b c Negishi, Ei-Ichi (1999). "A profile of Professor Richard F. Heck". Journal of Organometallic Chemistry. 576 (1–2): xv–xvi. doi:10.1016/S0022-328X(98)01136-X.
  4. ^ a b Heck, Richard F.; Breslow, David S. (1960). "Allylcobalt Carbonyls". Journal of the American Chemical Society. 82 (3): 750–751. doi:10.1021/ja01488a067.
  5. ^ a b Heck, Richard F.; Breslow, David S. (1961). "The Reaction of Cobalt Hydrotetracarbonyl with Olefins". Journal of the American Chemical Society. 83 (19): 4023–4027. doi:10.1021/ja01480a017.
  6. ^ Heck, Richard F. (1968). "Acylation, methylation, and carboxyalkylation of olefins by Group VIII metal derivatives". Journal of the American Chemical Society. 90 (20): 5518–5526. doi:10.1021/ja01022a034. and six further articles, pages 5526–5548
  7. ^ Mizoroki, Tsutomu; Mori, Kunio; Ozaki, Atsumu (1971). "Arylation of Olefin with Aryl Iodide Catalyzed by Palladium". Bulletin of the Chemical Society of Japan. 44 (2): 581. doi:10.1246/bcsj.44.581.
  8. ^ Heck, R. F.; Nolley, J. P. (1972). "Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides". The Journal of Organic Chemistry. 37 (14): 2320–2322. doi:10.1021/jo00979a024.
  9. ^ Beletskaya, Irina P.; Cheprakov, Andrei V. (2000). "The Heck Reaction as a Sharpening Stone of Palladium Catalysis". Chemical Reviews. 100 (8): 3009–3066. doi:10.1021/cr9903048. PMID 11749313.
  10. ^ Mc Cartney, Dennis; Guiry, Patrick J. (2011). "The asymmetric Heck and related reactions". Chemical Society Reviews. 40 (10): 5122–5150. doi:10.1039/C1CS15101K. PMID 21677934.
  11. ^ Heck, Richard F. (1982). "Palladium-Catalyzed Vinylation of Organic Halides". Organic Reactions. pp. 345–390. doi:10.1002/0471264180.or027.02. ISBN 0471264180.
  12. ^ Link, J. T. (2002). "The Intramolecular Heck Reaction". Organic Reactions. pp. 157–561. doi:10.1002/0471264180.or060.02. ISBN 0471264180.
  13. ^ Oestreich, Martin, ed. (2009). The Mizoroki-Heck Reaction. Chichester, United Kingdom: Wiley. pp. 1–608. ISBN 9780470033944. OCLC 233173519.
  14. ^ Johansson Seechurn, Carin C. C.; Kitching, Matthew O.; Colacot, Thomas J.; Snieckus, Victor (2012). "Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize". Angewandte Chemie International Edition. 51 (21): 5062–5085. doi:10.1002/anie.201107017. PMID 22573393.
  15. ^ Harrington, Peter J.; Lodewijk, Eric (1997). "Twenty Years of Naproxen Technology". Organic Process Research & Development. 1: 72–76. doi:10.1021/op960009e.
  16. ^ Kodama, Koichiro; Fukuzawa, Seketsu; Nakayama, Hiroshi; Sakamoto, Kensaku; Kigawa, Takanori; Yabuki, Takashi; Matsuda, Natsuko; Shirouzu, Mikako; Takio, Koji; Yokoyama, Shigeyuki; Tachibana, Kazuo (2007). "Site-Specific Functionalization of Proteins by Organopalladium Reactions". ChemBioChem. 8 (2): 232–238. doi:10.1002/cbic.200600432. PMID 17195252. S2CID 46474691.
  17. ^ Lim, Reyna K. V.; Li, Nan; Ramil, Carlo P.; Lin, Qing (2014). "Fast and Sequence-Specific Palladium-Mediated Cross-Coupling Reaction Identified from Phage Display". ACS Chemical Biology. 9 (9): 2139–2148. doi:10.1021/cb500443x. PMC 4168780. PMID 25025771.
  18. ^ Sonogashira, Kenkichi; Tohda, Yasuo; Hagihara, Nobue (1975). "A convenient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines". Tetrahedron Letters. 16 (50): 4467–4470. 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. ^ . C&EN. 84 (6): 34–38. February 6, 2006. Archived from the original on August 6, 2007..
  21. ^ . Nobelprize.org. October 7, 2010. Archived from the original on October 14, 2010. Retrieved October 7, 2010.
  22. ^ . 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. . Inquirer.net. Archived from the original on October 10, 2010.
  25. ^ Nicholas St. Fleur (October 15, 2015). "Richard F. Heck, Chemist Who Revolutionized Drug Development, Dies at 84". New York Times. Retrieved October 16, 2015.
  26. ^ Francisco, Rosemarie (October 10, 2015). . 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 edit

 
Wikimedia Commons has media related to Richard Fred Heck.

April 08, 2024
richard, heck, richard, frederick, heck, august, 1931, october, 2015, american, chemist, noted, discovery, development, heck, reaction, which, uses, palladium, catalyze, organic, chemical, reactions, that, couple, aryl, halides, with, alkenes, analgesic, napro. Richard Frederick Heck August 15 1931 October 9 2015 was an American chemist noted for the discovery and development of the Heck reaction which uses palladium to catalyze 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 Richard F HeckHeck in 2010BornRichard Frederick Heck 1931 08 15 August 15 1931Springfield Massachusetts U S DiedOctober 9 2015 2015 10 09 aged 84 Manila PhilippinesNationalityAmericanAlma materUCLA BS PhD Known forHeck reactionSpouseSocorro Nardo Heck died 2012 AwardsGlenn T Seaborg Medal 2011 Nobel Prize in Chemistry 2010 Scientific careerFieldsChemistryInstitutionsUniversity of DelawareHerculesETH ZurichDe La Salle UniversityDoctoral advisorSaul WinsteinFor his work in palladium catalyzed coupling reactions and organic synthesis Heck was awarded the 2010 Nobel Prize in Chemistry shared with the Japanese chemists Ei ichi Negishi and Akira Suzuki 1 Contents 1 Early life and education 2 Career 2 1 Palladium catalyzed coupling reactions 3 Later life and death 4 Honorary degrees 5 See also 6 References 7 External linksEarly life and education editHeck was born in Springfield Massachusetts in 1931 2 He moved to Los Angeles when eight years old and later attended the University of California Los Angeles UCLA gaining a bachelor s degree in 1952 and then a Ph D in 1954 working under the supervision of Saul Winstein on the chemistry of aryl sulfonates After postdoctoral research at the ETH in Zurich Switzerland with Vladimir Prelog and then back at UCLA Heck took a position with the Hercules Corporation in Wilmington Delaware in 1956 working initially on polymer chemistry 3 Career edit nbsp Peter Diamond Dale T Mortensen Christopher A Pissarides Konstantin Novoselov Andre Geim 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 organometallic chemistry including work with David S Breslow on organocobalt reactions 4 5 This led to the development of the Heck reaction which began with his investigation during the late 1960s of the coupling of 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 p allyl metal complex 4 and the first to elucidate the mechanism of alkene hydroformylation 5 Palladium catalyzed coupling reactions edit See also Palladium catalyzed coupling reactions Heck s work set the stage for a variety of other palladium catalyzed coupling reactions including those of aryl halides with derivatives of boronic acid Suzuki Miyaura coupling organotin reagents Stille coupling organomagnesium compounds Kumada Corriu coupling silanes Hiyama coupling and organozincs Negishi coupling as well as with amines Buchwald Hartwig amination and alcohols 14 These palladium catalyzed coupling reactions are now widely practiced in organic synthesis including for the manufacture of 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 editHeck 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 Wallace H Carothers Award which recognizes creative applications of chemistry that have had substantial commercial impact He was awarded the 2006 Herbert C Brown Award for creative research in synthetic methods 19 20 On October 6 2010 the Swedish Royal Academy of Sciences awarded Heck the Nobel Prize in Chemistry which he shared with Ei ichi Negishi and 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 editHeck received honorary doctorates from the Faculty of Pharmacy at Uppsala University in 2011 27 and De La Salle University in 2012 28 See also editMakoto Kumada Ei ichi Negishi Akira Suzuki Kenkichi SonogashiraReferences edit a b Press release 6 October 2010 Royal Swedish Academy of Sciences retrieved October 6 2010 Finucane Martin October 6 2010 Nobel Prize winner is Springfield native Boston Globe a b c Negishi Ei Ichi 1999 A profile of Professor Richard F Heck Journal of Organometallic Chemistry 576 1 2 xv xvi doi 10 1016 S0022 328X 98 01136 X a b Heck Richard F Breslow David S 1960 Allylcobalt Carbonyls Journal of the American Chemical Society 82 3 750 751 doi 10 1021 ja01488a067 a b Heck Richard F Breslow David S 1961 The Reaction of Cobalt Hydrotetracarbonyl with Olefins Journal of the American Chemical Society 83 19 4023 4027 doi 10 1021 ja01480a017 Heck Richard F 1968 Acylation methylation and carboxyalkylation of olefins by Group VIII metal derivatives Journal of the American Chemical Society 90 20 5518 5526 doi 10 1021 ja01022a034 and six further articles pages 5526 5548 Mizoroki Tsutomu Mori Kunio Ozaki Atsumu 1971 Arylation of Olefin with Aryl Iodide Catalyzed by Palladium Bulletin of the Chemical Society of Japan 44 2 581 doi 10 1246 bcsj 44 581 Heck R F Nolley J P 1972 Palladium catalyzed vinylic hydrogen substitution reactions with aryl benzyl and styryl halides The Journal of Organic Chemistry 37 14 2320 2322 doi 10 1021 jo00979a024 Beletskaya Irina P Cheprakov Andrei V 2000 The Heck Reaction as a Sharpening Stone of Palladium Catalysis Chemical Reviews 100 8 3009 3066 doi 10 1021 cr9903048 PMID 11749313 Mc Cartney Dennis Guiry Patrick J 2011 The asymmetric Heck and related reactions Chemical Society Reviews 40 10 5122 5150 doi 10 1039 C1CS15101K PMID 21677934 Heck Richard F 1982 Palladium Catalyzed Vinylation of Organic Halides Organic Reactions pp 345 390 doi 10 1002 0471264180 or027 02 ISBN 0471264180 Link J T 2002 The Intramolecular Heck Reaction Organic Reactions pp 157 561 doi 10 1002 0471264180 or060 02 ISBN 0471264180 Oestreich Martin ed 2009 The Mizoroki Heck Reaction Chichester United Kingdom Wiley pp 1 608 ISBN 9780470033944 OCLC 233173519 Johansson Seechurn Carin C C Kitching Matthew O Colacot Thomas J Snieckus Victor 2012 Palladium Catalyzed Cross Coupling A Historical Contextual Perspective to the 2010 Nobel Prize Angewandte Chemie International Edition 51 21 5062 5085 doi 10 1002 anie 201107017 PMID 22573393 Harrington Peter J Lodewijk Eric 1997 Twenty Years of Naproxen Technology Organic Process Research amp Development 1 72 76 doi 10 1021 op960009e Kodama Koichiro Fukuzawa Seketsu Nakayama Hiroshi Sakamoto Kensaku Kigawa Takanori Yabuki Takashi Matsuda Natsuko Shirouzu Mikako Takio Koji Yokoyama Shigeyuki Tachibana Kazuo 2007 Site Specific Functionalization of Proteins by Organopalladium Reactions ChemBioChem 8 2 232 238 doi 10 1002 cbic 200600432 PMID 17195252 S2CID 46474691 Lim Reyna K V Li Nan Ramil Carlo P Lin Qing 2014 Fast and Sequence Specific Palladium Mediated Cross Coupling Reaction Identified from Phage Display ACS Chemical Biology 9 9 2139 2148 doi 10 1021 cb500443x PMC 4168780 PMID 25025771 Sonogashira Kenkichi Tohda Yasuo Hagihara Nobue 1975 A convenient synthesis of acetylenes Catalytic substitutions of acetylenic hydrogen with bromoalkenes iodoarenes and bromopyridines Tetrahedron Letters 16 50 4467 4470 doi 10 1016 S0040 4039 00 91094 3 Richard Heck professor emeritus and Nobel laureate dies udel edu October 10 2015 Retrieved August 22 2022 2006 ACS National Award Winners C amp EN 84 6 34 38 February 6 2006 Archived from the original on August 6 2007 Richard F Heck Interview Nobelprize org October 7 2010 Archived from the original on October 14 2010 Retrieved October 7 2010 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 Suarez Larissa Mae October 7 2010 US scientist residing in Philippines wins 2010 chemistry Nobel GMANews tv Quismundo Tarra He s the only Nobel winner living in RP Inquirer net Archived from the original on October 10 2010 Nicholas St Fleur October 15 2015 Richard F Heck Chemist Who Revolutionized Drug Development Dies at 84 New York Times Retrieved October 16 2015 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 Honorary Doctors of the Faculty of Pharmacy uu se Retrieved May 28 2018 Make Life Simple Through Chemistry Nobel Laureate Dr Richard Heck s Goal nast ph Retrieved May 28 2018 External links edit nbsp Wikimedia Commons has media related to Richard Fred Heck Department of Chemistry and Biochemistry at the University of Delaware Richard F Heck on Nobelprize org nbsp Retrieved from https en wikipedia org w index php title Richard F Heck amp oldid 1217694912, wikipedia, wiki, book, books, library,

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