Journal of the American Chemical Society
ARTICLE
’ ACKNOWLEDGMENT
Alper, H. Org. Lett. 2008, 10, 4903. (n) Vieira, T. O.; Meaney, L. A.; Shi,
Y.-L.; Alper, H. Org. Lett. 2008, 10, 4899.
(7) For selected examples see: (a) Wu, X. F.; Neumann, H.; Beller,
M. Angew. Chem. Int. Ed. 2010, 49, 5284. (b) Wu, X. F.; Neumann, H.;
Spannenberg, A.; Schulz, T.; Jiao, H.; Beller, M. J. Am. Chem. Soc. 2010,
132, 14596. (c) Wu, X.; Nilsson, P.; Larhed, M. J. Org. Chem. 2005,
70, 346.
We are deeply appreciative of generous financial support from
the Danish National Research Foundation, The Danish Natural
Science Research Council, the Carlsberg Foundation and Aarhus
University. We also thank Dr. Mette L. H. Mantel for her work on
the initial optimization studies of the aminocarbonylations with
2-pyridyl tosylates using balloons as the CO-reservoir.
(8) For selected examples see: (a) Khedkar, M. V.; Tambade, P. J.;
Qureshi, Z. S.; Bhanage, B. M. Eur. J. Org. Chem. 2010, 6981. (b) Andrus,
M. B.; Ma, Y.; Zang, Y.; Song, C. Tetrahedron Lett. 2002, 43, 9137. (c)
O’Keefe, B. M.; Simmons, N.; Martin, S. F. Org. Lett. 2008, 10, 5301. (d)
Qureshi, Z. S.; Deshmukh, K. M.; Tambade, P. J.; Bhanage, B. M. Synthesis
2011, 243. (e) Tambade, P. J.; Patil, Y. P.; Panda, A. G.; Bhanage, B. M. Eur.
J. Org. Chem. 2009, 3022. (f) Pirez, C.; Dheur, J.; Sauthier, M.; Castanet, Y.;
Mortreux, A. Synlett 2009, 1745. (g) Couve-Bonnaire, S.; Carpentier, J.-F.;
Mortreux, A.; Castanet, Y. Tetrahedron 2003, 59, 2793. (h) Maerten, E.;
Hassouna, F.; Couve-Bonnaire, S.; Mortreux, A.; Carpentier, J.-F.; Castanet,
Y. Synlett 2003, 12, 1874. (i) Couve-Bonnaire, S.; Carpentier, J.-F.;
Mortreux, A.; Castanet, Y. Tetrahedron Lett. 2001, 42, 3689. (j) Larini, P.;
Guarna, A.; Ernesto, G. O. Org. Lett. 2006, 8, 781. (k) Wu, X.-F.; Neumann,
H.; Beller, M. Tetrahedron Lett. 2010, 47, 6146. (l) Neumann, H.;
Brennf€uhrer, A.; Beller, M. Chem.—Eur. J. 2008, 14, 3645. (m) Ishiyama,
T.; Kizaki, H.; Hayashi, T.; Suzuki, A.; Miyaura, N. J. Org. Chem. 1998,
63, 4726.
(9) For selected examples see: (a) Wu, X.-F.; Sundararaju, B.; Neumann,
H.; Dixneuf, P. H.; Beller, M. Chem.—Eur. J. 2010, 17, 106. (b) Liu, J.; Chen,
J.; Xia, C. J. Catal. 2008, 253, 50. (c) Lizuka, M.; Kondo, Y. Eur. J. Org. Chem.
2007, 5180. (d)Rahman, M. T.;Fukuyama, T.;Kamata, N.;Sato., M.;Ryu, I.
Chem. Commun. 2006, 2236. (e) Fusano, A.; Fukuyama, T.; Nishitani, S.;
Inouye, T.; Ryu, I. Org. Lett. 2010, 12, 2410. (f) Fukuyama, T.; Yamaura, R.;
Ryu, I. Can. J. Chem. 2005, 83, 711. (g) Wu, X.-F.; Neumann, M.; Beller, M.
Chem.—Eur. J. 2010, 16, 12104.(h) Ahmed, M. S. M.; Mori, A. Org. Lett.
2003, 5, 3057, and references therein.
’ REFERENCES
(1) For reviews on CO in transition metal chemistry see: (a) Grigg,
R.; Mutton, S. P. Tetrahedron 2010, 66, 5515. (b) Brennf€uhrer, A.;
Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114. (c)
Bernard, C. F. Organometallics 2008, 27, 5402. (d) Omae, I. Coord.
Chem. Rev. 2011, 255, 139. (e) Morimoto, T.; Kakiuchi, K. Angew.
Chem., Int. Ed. 2004, 43, 5580. (f) Yamamoto, A.; Kayaki, Y.; Nagayama,
K.; Shimizu, I. Synlett 1999, 7, 925. (g) Brunet, J.-J.; Chauvin, R. Chem.
Soc. Rev. 1995, 24, 89. (h) Skoda-F€oldes, R.; Kollꢀar, L. Curr. Org. Chem.
2002, 6, 1097. (i) Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpainter,
C. W. J. Mol. Catal. A: Chem. 1995, 104, 17. (j) Brennf€uhrer, A.;
Neumann, H.; Beller, M. ChemCatChem 2009, 1, 28. (k) Ryu, I.; Sonoda,
N. Angew. Chem., Int. Ed. 1996, 35, 1050.
(2) For selected references on, hydroformylations see: (a) Jennerjahn,
R.; Piras, I.; Jackstell, R.; Franke, R.; Wiese, K. D.; Beller, M. Chem.—Eur. J.
2009, 15, 6383–6388. (b) No onan, G. M.; Cobley, C. J.; Lebl, T.; Clarke,
M. L. Chem.—Eur. J. 2010, 16, 12788. (c) Ashfield, L.; Barnard, C. F. J. Org.
Process Res. Dev. 2007, 11, 39. Hydroesterfications, see: (d) Kiss, G. Chem.
Rev. 2001, 101, 3435. (e) Yang, J.; Yuan, Y. Catal. Lett. 2009, 131, 643.
Yokota, K.; Tatamidani, H.; Fukumoto, Y.; Chatani, N. Org. Lett. 2003,
5, 4329. (f) Hiyama, T.; Wakasa, N.; Kusumoto, T. Synlett 1991, 569.
(g) Estorach, C. T.; Masdeu-Bultꢀo, A. M. Catal. Lett. 2008, 122, 76.
Alcohols: Hahn, H.-D.; D€ambkes, G.; Rupprich, N. ;Ullmann’s Encyclopedia
of Industrial Chemistry; Wiley-VCH: Weinheim, 2005. Other, see:
(h) Sheldon, R. A. J. Mol. Catal. A: Chem. 1996, 107, 75, and references
therein.
(10) Constable, D. J.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.;
Leazer, J. L., Jr.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.;
Wells, A.; Zaks, A.; Zhang, T. Y. Green Chem. 2007, 9, 411.
(11) Maitlis, P.; Haynes, A. In Metal-Catalysis in Industrial Organic
Processes; RSC Publishing: Cambridge, U.K, 2006; pp 114ꢀ162.
(12) For selected recent references, see: (a) Martinelli, J. R.; Watson,
D. A.; Freckmann, D. M. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem.
2008, 73, 7102. (b) Martinelli, J. R.; Clark, T. P.; Watson, D. A.; Munday,
R. H.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 8460. (c)
Martinelli, J. R.; Freckmann, D. M. M.; Buchwald, S. L. Org. Lett. 2006,
8, 4843. (d) Cao, H.; Vieira, T. O.; Alper, H. Org. Lett. 2010, 13, 11.(e)
Munday, R. H.; Martinelli, J. R.; Buchwald, S. L. 2008, 130, 2754. (f) Hu,
Y.; Liu, J.; L€u, Z.; Luo, X.; Zhang, H.; Lan, Y.; Lei, A. J. Am. Chem. Soc.
2010, 132, 3153, and references therein.
(13) For selected examples on alternative CO-sources: Alkyl for-
mates, (a) Schareina, T.; Zapf, A.; Cottꢀe; Gotta, M.; Beller, M. Adv.
Synth. Catal. 2010, 352, 1205. Molybdenum carbonyl derivatives, (b)
Lesma, G.; Sacchetti, A.; Silvani, A. Synthesis 2006, 4, 594. (c) Wannberg,
J.; Larhed, M. J. Org. Chem. 2003, 68, 5750. (d) Wu, X.; Ekegren, J. K.;
Larhed, M. Organometallics 2006, 25, 1434. (e) Odell, L. R.; S€avmarker,
J.; Larhed, M. Tetrahedron Lett. 2008, 49, 6115. (f) Roberts, B.; Liptrot,
D.; Alcaraz, L.; Luker, T.; Stocks, M. J. Org. Lett. 2010, 12, 4280.(g)
Modern Carbonylation Methods; Kolla, L., Ed.; Wiley & Sons: Germany,
2008. Chapter 4 written by Johan Wannberg and Mats Larhed. (h)
Wieckowska, A.; Fransson, R.; Odell, L. R.; Larhed, M. J. Org. Chem.
2011, 76, 978. Glycose: (i) Ikeda, K.; Morimoto, T.; Kakiuchi, K. J. Org.
Chem. 2010, 75, 6279. Oxalyl chloride: (j) Rao, M. L. N.; Venkatesh, V.;
Dasgupta, P. Tetrahedron Lett. 2010, 51, 4975. Lithium formate: (k)
Elmore, C. S.; Dean, D. C.; Melillo, D. G. J. Labelled Compd. Radiopharm.
2000, 43, 1135. (l) Simeone, J. P.; Braun, M. P.; Liu, L.; Natarajan, S. R.
J. Labelled Compd. Radiopharm. 2010, 53, 511. (m) Elmore, C. S.; Dorff,
P. N.; Heys, J. R. J. Labelled Compd. Radiopharm. 2010, 53, 787.
Aldehydes: (n) Morimoto, T.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. J. Am.
Chem. Soc. 2002, 124, 3806. (o) Fuji, K.; Morimoto, T.; Tsutsumi, K.;
Kaiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409.(p) Morimoto, T.; Fujioka,
(3) Catalytic Synthesis of Alkene-Carbon Monoxide Copolymers and
Cooligomers; Sen, A., Ed.; Springer: Dordrecht, The Netherlands, 2003.
(4) Schoenberg, A.; Bartoletti, I.; Heck, R. F. J. Org. Chem. 1974,
39, 3318. (b) Schoenberg, A.; Heck, R. F. J. Org. Chem. 1974, 39, 3327.
(5) For selected examples see: (a) Zapf, A.; Beller, M. Top. Catal.
2002, 19, 101. (b) Wu, X.-F.; Neumann, H.; Beller, M. ChemCatChem
2010, 2, 509. (c) Albaneze-Walker, J.; Bazaral, C.; Leavey, T.; Dormer,
P. G.; Murry, J. A. Org. Lett. 2004, 6, 2097. (d) Munday, R. H.; Martinelli,
J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 2754. (e) Watson,
D. A.; Fan, X.; Buchwald, S. L. J. Org. Chem. 2008, 73, 7096.
(f) M€agerlein, W.; Indolese, A. F.; Bellers, M. Angew. Chem., Int. Ed.
2001, 40, 2856. (g) M€agerlein, W.; Indolese, A. F.; Beller, M.
J. Organomet. Chem. 2002, 641, 30. (h) Arthuis, M.; Lecup, A.; Roulland,
E. Chem. Commun. 2010, 46, 7810. (i) Beller, M; M€agerlein, W.;
Indolese, A. F.; Fischer, C. Synthesis 2001, 7, 1098.
(6) For selected examples see: (a) Martinelli, J. R.; Watson, D. A.;
Freckmann, D. M. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem.
2008, 7102. (b) Martinelli, J. R.; Watson, D. A.; Munday, R. H.; Buchwald,
S. L. Angew. Chem., Int. Ed. 2007, 46, 8460. (c) Yang, Q.; Cao, H.;
Robertson, A.; Alper, H. J. Org. Chem. 2010, 75, 6297. (d) Tadd, A. C.;
Matsuno, A.; Fielding, M. R.; Willis, M. C. Org. Lett. 2009, 11, 583. (e) Cao,
H.; Alper, H. Org. Lett. 2010, 12, 4126. (f) Deagostino, A.; Larini, P.;
Ernesto, G. O.; Pizzuto, L.; Prandi, C.; Venturello, P. J. Org. Chem. 2008,
73, 1941. (g) Wu, X.-F.; Neumann, H.; Beller, M. Chem.—Eur. J. 2010,
16, 9750. (h) Neumann, H.; Brennf€uhrer, A.; Gross, P.; Riermeier, T.;
Almena, J.; Beller, M. Adv. Synth. Catal. 2006, 348, 1255. (i) Qu, B.; Haddad,
N.; Han, Z. S.; Rodriguez, S.; Lorenz, J. C.; Grinberg, N.; Lee, H.; Busacca,
C. A.; Krishnamurthy, D.; Senanayake, C. H. Tetrahedron Lett. 2009,
50, 6126. (j) Brennf€uhrer, A.; Neumann, H.; Pews-Davtyan, A.; Beller,
M. Eur. J. Org. Chem. 2009, 38. (k) Kumar, K.; Zapf, A.; Michalik, D.; Tillack,
A.; Heinrich, T.; B€ottcher, H.; Arlt, M.; Beller, M. Org. Lett. 2004, 6, 7. (l)
Cao, H.; McNamee, L.; Alper, H. Org. Lett. 2008, 10, 5281. (m) Zheng, Z.;
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