26.05.2014 Views

The 2010 Nobel Prize in Chemistry - Platinum Metals Review

The 2010 Nobel Prize in Chemistry - Platinum Metals Review

The 2010 Nobel Prize in Chemistry - Platinum Metals Review

SHOW MORE
SHOW LESS

Create successful ePaper yourself

Turn your PDF publications into a flip-book with our unique Google optimized e-Paper software.

doi:10.1595/147106711X558301<br />

•Plat<strong>in</strong>um <strong>Metals</strong> Rev., 2011, 55, (2)•<br />

In order to address the issue of residual palladium<br />

<strong>in</strong> the f<strong>in</strong>al product, several solid-supported<br />

preformed palladium complexes have been developed<br />

and launched onto the catalyst market<br />

(54–56).<br />

Conclusions<br />

Palladium-catalysed cross-coupl<strong>in</strong>g is of great importance<br />

to real world applications <strong>in</strong> the pharmaceutical,<br />

agrochemicals, f<strong>in</strong>e chemicals and electronics<br />

<strong>in</strong>dustries. <strong>The</strong> area has developed quite rapidly<br />

beyond the work of Heck, Negishi and Suzuki,<br />

though all three reactions are widely used. Academic<br />

groups such as those of Beller, Buchwald, Fu, Hartwig<br />

and Nolan as well as <strong>in</strong>dustrial groups such as that<br />

at Johnson Matthey, are now develop<strong>in</strong>g the field even<br />

further. Buchwald-Hartwig coupl<strong>in</strong>g has become particularly<br />

important for develop<strong>in</strong>g compounds conta<strong>in</strong><strong>in</strong>g<br />

carbon–nitrogen bonds for applications <strong>in</strong><br />

<strong>in</strong>dustry, as well as α-arylation of carbonyl compounds<br />

such as ketones, esters, amides, aldehydes<br />

etc., and nitriles (57). <strong>The</strong> significant growth of crosscoupl<strong>in</strong>g<br />

reactions can be summarised <strong>in</strong> Professor<br />

K. C. Nicolaou’s words:<br />

“In the last quarter of the 20th century, a new<br />

paradigm for carbon–carbon bond formation has<br />

emerged that has enabled considerably the prowess<br />

of synthetic organic chemists to assemble complex<br />

molecular frameworks and has changed the way<br />

we th<strong>in</strong>k about synthesis”(58).<br />

More detailed articles summaris<strong>in</strong>g the history of<br />

cross-coupl<strong>in</strong>g <strong>in</strong> the context of the <strong>2010</strong> <strong>Nobel</strong> <strong>Prize</strong><br />

<strong>in</strong> <strong>Chemistry</strong> with an outlook on the future of crosscoupl<strong>in</strong>g<br />

will be published elsewhere (59, 60).<br />

Glossary<br />

Ligand<br />

A ta -Phos<br />

Cy<br />

dppf<br />

dtbpf<br />

Np<br />

Ph<br />

Q-Phos<br />

t Bu<br />

Name<br />

p-dimethylam<strong>in</strong>ophenyl(di-tert-butyl)phosph<strong>in</strong>e<br />

cyclohexyl<br />

1,1′-bis(diphenylphosph<strong>in</strong>o)ferrocene<br />

1,1′-bis(di-tert-butylphosph<strong>in</strong>o)ferrocene<br />

neopentyl<br />

phenyl<br />

1,2,3,4,5-pentaphenyl-1′-(di-tert-butylphosph<strong>in</strong>o)ferrocene<br />

tert-butyl<br />

References<br />

1 T. Colacot, Plat<strong>in</strong>um <strong>Metals</strong> Rev., 2008, 52, (3), 172<br />

2 “Metal-Catalyzed Cross-Coupl<strong>in</strong>g Reactions”, 2nd Edn.,<br />

eds. A. de Meijere and F. Diederich, Wiley-VCH,<br />

We<strong>in</strong>heim, Germany, 2004<br />

3 C. Barnard, Plat<strong>in</strong>um <strong>Metals</strong> Rev., 2008, 52, (1), 38<br />

4 ‘Scientific Background on the <strong>Nobel</strong> <strong>Prize</strong> <strong>in</strong> <strong>Chemistry</strong><br />

<strong>2010</strong>: Palladium-Catalyzed Cross Coupl<strong>in</strong>gs <strong>in</strong> Organic<br />

Synthesis’, <strong>The</strong> Royal Swedish Academy of Sciences,<br />

Stockholm, Sweden, 6th October, <strong>2010</strong>: http://<br />

nobelprize.org/nobel_prizes/chemistry/laureates/<strong>2010</strong>/sci.<br />

html (Accessed on 24 January 2011)<br />

5 T. Mizoroki, K. Mori and A. Ozaki, Bull. Chem. Soc. Jpn.,<br />

1971, 44, (2), 581<br />

6 K. Mori, T. Mizoroki and A. Ozaki, Bull. Chem. Soc. Jpn.,<br />

1973, 46, (5), 1505<br />

7 R. F. Heck, J. Am. Chem. Soc., 1968, 90, (20), 5518<br />

8 R. F. Heck and J. P. Nolley, J. Org. Chem., 1972, 37,<br />

(14), 2320<br />

9 H. A. Dieck and R. F. Heck, J. Am. Chem. Soc., 1974,<br />

96, (4), 1133<br />

10 E. Negishi and S. Baba, J. Chem. Soc., Chem. Commun.,<br />

1976, (15), 596b<br />

11 E. Negishi, A. O. K<strong>in</strong>g and N. Okukado, J. Org. Chem.,<br />

1977, 42, (10), 1821<br />

12 A. O. K<strong>in</strong>g, N. Okukado and E. Negishi, J. Chem. Soc.,<br />

Chem. Commun., 1977, (19), 683<br />

13 J. F. Fauvarque and A. Jutand, J. Organomet. Chem.,<br />

1977, 132, (2), C17<br />

14 K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka,<br />

S. Kodama, I. Nakajima, A. M<strong>in</strong>ato and M. Kumada, Bull.<br />

Chem. Soc. Jpn., 1976, 49, (7), 1958<br />

15 K. Tamao, Y. Kiso, K. Sumitani and M. Kumada, J. Am.<br />

Chem. Soc., 1972, 94, (26), 9268<br />

16 K. Tamao, K. Sumitani and M. Kumada, J. Am. Chem.<br />

Soc., 1972, 94, (12), 4374<br />

17 M. Kumada, <strong>in</strong> “Organotransition Metal <strong>Chemistry</strong>”, eds.<br />

Y. Ishii and M. Tsutsui, Plenum Press, New York, USA,<br />

1975, p. 211<br />

18 R. J. P. Corriu and J. P. Masse, J. Chem. Soc., Chem.<br />

Commun., 1972, (3), 144a<br />

89 © 2011 Johnson Matthey

Hooray! Your file is uploaded and ready to be published.

Saved successfully!

Ooh no, something went wrong!