R.S. Ramo´n et al. / Tetrahedron 65 (2009) 1767–1773
1773
Commun. 2006, 2048–2050; (c) Correa, A.; Marion, N.; Fensterbank, L.; Mal-
acria, M.; Nolan, S. P.; Cavallo, L. Angew. Chem., Int. Ed. 2008, 47, 718–721; (d) de
Fre´mont, P.; Marion, N.; Nolan, S. P. J. Organomet. Chem. 2009, 694. doi:10.1016/
j.jorganchem.2008.10.047; (e) Gourlaouen, C.; Marion, N.; Nolan, S. P.; Maseras,
F. Org. Lett. 2009, 11, 81–84; (f) Marion, N.; Lemie`re, G.; Correa, A.; Costabile, C.;
Ramo´n, R. S.; Moreau, X.; de Fre´mont, P.; Dahmane, R.; Hours, A.; Lesage, D.;
Tabet, J.-C.; Goddard, J.-P.; Gandon, V.; Cavallo, L.; Fensterbank, L.; Malacria, M.;
Nolan, S. P. Chem.dEur. J. 2009, 15. doi:10.1002/chem.200801387
is an ICREA Research Professor. NM (2007FI_A 01466) and RSR
(2008FI 01047) received pre-doctoral fellowships by the AGAUR.
NM thanks Umicore for a Ph.D. award.
References and notes
1. (a) For a review on Diels–Alder in total synthesis, see: Nicolaou, K. C.; Snyder, S.
A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668–
1698; (b) Cesati, R. R., III; de Armas, J.; Hoveyda, A. H. J. Am. Chem. Soc. 2004,
126, 96–101.
´
´
´
23. Marion, N.; Dıez-Gonzalez, S.; de Fremont, P.; Noble, A. R.; Nolan, S. P. Angew.
Chem., Int. Ed. 2006, 45, 3647–3650.
24. (a) For AuIII hydration of propargylic ethers followed by elimination, see: Fu-
kuda, Y.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 2013–2015; (b) The formation
of the hydration product 2ra raises questions about a mechanism involving
a hydration of the triple bond followed by the elimination of water. As our
catalytic system shows with terminal alkynes only poor to moderate conver-
sions into the Meyer–Schuster products, we suggest under our reaction con-
ditions a different reactivity of terminal alkynes compared to internal alkynes.
For the observation of such a dichotomy, see: Marion, N.; Ra´mon, R. S.; Nolan,
S. P. J. Am. Chem. Soc. 2009, 131. doi:10.1021/ja809403e
´
´
´
2. (a) Padron, J. M.; Miranda, P. O.; Padron, J. I.; Martın, V. S. Bioorg. Med. Chem.
Lett. 2006, 16, 2266–2269; (b) Robinson, T. P.; Ehlers, T.; Hubbard, R. B., IV; Bai,
X.; Arbiser, J. L.; Goldsmith, D. J.; Bowen, J. P. Bioorg. Med. Chem. Lett. 2003, 13,
115–117.
3. For reviews on cyclopropanation and cyclopropanes, see: (a) Reissig, H.-U.;
Zimmer, R. Chem. Rev. 2003, 103, 1151–1196; (b) Brookhart, M.; Studabaker,
W. B. Chem. Rev. 1987, 87, 411–432; (c) Rubin, M.; Rubina, M.; Gevorgyan, V.
Chem. Rev. 2007, 107, 3117–3179; (d) Carey, F. A.; Sundberg, R. J. Advanced Or-
ganic Chemistry Part B: Reactions and Synthesis, 4th ed.; Kluver, Academic/
Plenum: New York, NY, 2001; pp 125, 625–634.
4. (a) Luo, J.; Xu, L.-W.; Hay, R. A. S.; Lu, J. Org. Lett. 2009, 11, 437–440; (b) Fur-
ukawa, T.; Shibata, N.; Mizuta, S.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem.,
Int. Ed. 2008, 47, 8051–8054.
5. For reviews, see: (a) Norton, J. A. Chem. Rev. 1942, 31, 319–523; (b) Corey, E. J.
Angew. Chem., Int. Ed. 2002, 41, 1650–1667; (c) Jørgensen, K. A. Angew. Chem.,
Int. Ed. 2000, 39, 3558–3588; (d) Winkler, J. D. Chem. Rev. 1996, 96, 167–176; (e)
Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry Part B: Reactions and
Synthesis, 4th ed.; Kluver Academic/Plenum: New York, NY, 2001; pp 331–376;
See also Ref. 1a.
6. For reviews, see: (a) Mahrwald, R. Chem. Rev. 1999, 99, 1095–1120; (b) Casiraghi,
G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929–1972; (c)
Palomo, C.; Oiarbide, M.; Garcı´a, J. M. Chem.dEur. J. 2002, 8, 36–44; (d) Smith,
M. B.; March, J. Advanced Chemistry: Reactions, Mechanisms, and Structure, 5th
ed.; Wiley: New York, NY, 2001; pp 1218–1223.
25. For rhodium catalyzed synthesis of indanones, see: (a) Shintani, R.; Okamoto,
K.; Hayashi, T. J. Am. Chem. Soc. 2005, 127, 2872–2873; (b) Shintani, R.; Yashio,
K.; Nakamura, T.; Okamoto, K.; Shimada, T.; Hayashi, T. J. Am. Chem. Soc. 2006,
128, 2772–2773; (c) Yamabe, H.; Mizuno, A.; Kusama, H.; Iwasawa, N. J. Am.
Chem. Soc. 2005, 127, 3248–3249.
26. (a) For a previous proposal of an aldehyde C–H bond activation by gold, see:
Skouta, R.; Li, C.-J. Angew. Chem., Int. Ed. 2007, 46, 1117–1119; (b) Hypothetic
mechanisms leading to indanone:
R
O
R
R
OH
[Au]
O
[Au]
[Au]
O
H
or
7. (a) Jones, G. Org. React. 1967, 15, 204–599; (b) Smith, M. B.; March, J. Advanced
Chemistry: Reactions, Mechanisms, and Structure, 5th ed.; Wiley: New York, NY,
2001; pp 1225–1228; See also Ref. 6.
8. (a) Iorga, B.; Eymery, F.; Mourie`s, V.; Savignac, P. Tetrahedron 1998, 54, 14637–
14677; (b) Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry Part B: Re-
actions and Synthesis, 4th ed.; Kluver Academic/Plenum: New York, NY, 2001;
pp 39–47.
R
[Au]
R
R
or
R
9. (a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259–281; (b) Trost, B. M.
Science 1991, 254, 1471–1477.
10. Rupe, H.; Kambli, E. Helv. Chim. Acta 1926, 9, 672.
O
OH
O
11. (a) Meyer, K. H.; Schuster, K. Chem. Ber. 1922, 55, 819–823; (b) Edens, M.;
Boerner, D.; Chase, C. R.; Nass, D.; Schiavelli, M. D. J. Org. Chem. 1977, 42, 3403–
3408.
[Au]
12. For ruthenium, see: (a) Cadierno, V.; Dı´ez, J.; Garcı´a-Garrido, S. E.; Gimeno, J.;
Nebra, N. Adv. Synth. Catal. 2006, 348, 2125–2132; (b) Cadierno, V.; Crochet, P.;
Gimeno, J. Synlett 2008, 1105–1124; (c) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y.
Tetrahedron Lett. 2002, 43, 7531–7533; (d) Trost, B. M.; Livingston, R. C. J. Am.
Chem. Soc. 1995, 117, 9586–9587; For rhodium, see: (e) Tanaka, K.; Shoji, T. Org.
Lett. 2005, 7, 3561–3563; For iridium, see: (f) Ma, D.; Lu, X. Tetrahedron Lett.
1989, 30, 2109–2112; For palladium, see: (g) Xiyan, L.; Jianguo, J.; Cheng, G.;
Wei, S. J. Organomet. Chem. 1992, 428, 259–266; For mercury, see: (h) Yadav, J.
S.; Prahlad, V.; Muralidhar, B. Synth. Commun.1997, 27, 3415–3418; For scandium,
see: (i) Engel, D. A.; Lopez, S. S.; Dudley, G. B. Tetrahedron 2008, 64, 6988–6996.
13. For recent reviews, see: (a) Jime´nez-Nu´ n˜ez, E.; Echavarren, A. M. Chem. Rev.
2008, 108, 3326–3350; (b) Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239–
3265; (c) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351–3378;
(d) Arcadi, A. Chem. Rev. 2008,108, 3266–3325; (e) For a review, focused on NHC–
Au catalysts, see: Marion, N.; Nolan, S. P. Chem. Soc. Rev. 2008, 37, 1776–1782.
14. For a review on propargylic esters in gold catalysis, see: Marion, N.; Nolan, S. P.
Angew. Chem., Int. Ed. 2007, 46, 2750–2752.
27. de Fre´mont, P.; Scott, N. M.; Stevens, E. D.; Nolan, S. P. Organometallics 2005, 24,
2411–2418.
28. For full characterization, see: (a) Taber, D. F.; Sheth, R. B.; Joshi, P. V. J. Org. Chem.
2005, 70, 2851–2854; (b) Zhang, Z.; Wang, Z. J. Org. Chem. 2006, 71, 7485–7487.
29. For full characterization, see Ref. 28b and (a) Masllorens, J.; Roglans, A.; Mor-
eno-Manas, M.; Parella, T. Organometallics 2004, 23, 2533–2540; (b) Yang, Q.;
Ma, S.; Li, J.; Xiao, F.; Xiong, H. Chem. Commun. 2006, 2495–2497.
30. For full characterization, see: Peach, P.; Cross, D. J.; Kenny, J. A.; Mann, I.;
Houson, I.; Campbell, L.; Walsgrove, T.; Wills, M. Tetrahedron 2006, 62, 1864–
1876.
31. For full characterization, see: (a) Baek, D.-J.; Daniels, S. B.; Reed, P. E.; Katze-
nellenbogen, J. A. J. Org. Chem. 1989, 54, 3963–3972; (b) Blakemore, P. R.; Ho, D.
K. H.; Nap, W. M. Org. Biomol. Chem. 2005, 3, 1365–1368.
32. For full characterization, see: Katritzky, A. R.; Wu, H.; Xie, L. J. Org. Chem. 1996,
61, 4035–4039.
33. For full characterization, see: Guan, B.; Xing, D.; Cai, G.; Wan, X.; Yu, N.; Fang,
Z.; Yang, L.; Shi, Z. J. Am. Chem. Soc. 2005, 127, 18004–18005.
34. For full characterization, see: Heasley, V. L.; Louie, T. J.; Luttrull, D. K.; Millar,
M. D.; Moore, H. B.; Nogales, D. F.; Sauerbrey, A. M.; Shevel, A. B.; Shibuya, T. Y.
J. Org. Chem. 1988, 53, 2199–2204.
35. For full characterization, see: Ley, S. V.; Mitchell, C.; Pears, D.; Ramarao, C.; Yu,
J.-Q.; Zhou, W. Org. Lett. 2003, 5, 4665–4668.
36. For full characterization, see: Chassaing, S.; Kumarraja, M.; Pale, P.; Sommer, J.
Org. Lett. 2007, 9, 3889–3892.
15. Yu, M.; Li, G.; Wang, S.; Zhang, L. Adv. Synth. Catal. 2007, 349, 871–875.
´
16. Marion, N.; Carlqvist, P.; Gealageas, R.; de Fremont, P.; Maseras, F.; Nolan, S. P.
Chem.dEur. J. 2007, 13, 6437–6451.
17. Georgy, M.; Boucard, V.; Campagne, J.-M. J. Am. Chem. Soc. 2005, 127, 14180–
14181.
18. Engel, D. A.; Dudley, G. B. Org. Lett. 2006, 8, 4027–4029.
19. Lopez, S.; Engel, D.; Dudley, G. Synlett 2007, 949–953.
20. Lee, S. I.; Baek, J. Y.; Sim, S. H.; Chung, Y. K. Synthesis 2007, 2107–2114.
21. Egi, M.; Yamaguchi, Y.; Fujiwara, N.; Akai, S. Org. Lett. 2008, 10, 1867–1870.
22. For our recent work on gold–NHCs in catalysis, see: (a) Marion, N.; Gealageas,
R.; Nolan, S. P. Org. Lett. 2007, 9, 2653–2656; (b) Marion, N.; de Fre´mont, P.;
`
Lemiere, G.; Stevens, E. D.; Fensterbank, L.; Malacria, M.; Nolan, S. P. Chem.