Journal of the American Chemical Society
Article
(c) Gansauer, A. Chem. Commun. 1997, 457. (d) Gansauer, A. Synlett
(10) Handa, Y.; Inanaga, J. Tetrahedron Lett. 1987, 28, 5717.
̈
̈
1997, 363. (e) Gansauer, A.; Moschioni, M.; Bauer, D. Eur. J. Org. Chem.
(11) Some alkynes and alkenes were applicable to the salt-free
reduction of MoCl5 and WCl6: (a) Larson, M. L.; Moore, F. W. Inorg.
Chem. 1964, 3, 285. (b) Allen, E. A.; Brisdon, B. J.; Fowles, G. W. A. J.
Chem. Soc. 1964, 4531. (c) Filippo, J. S.; Sowinski, A. F.; Romano, L. J. J.
Am. Chem. Soc. 1975, 97, 1599. (d) Kovacic, P.; Brace, N. O. J. Am.
Chem. Soc. 1984, 76, 5491. (e) Berglund, M.; Andersson, C.; Larsson, R.
J. Organomet. Chem. 1986, 314, 61. (f) Persson, C.; Andersson, C.
Polyhedron 1991, 10, 2089. (g) Persson, C.; Andersson, C. Inorg. Chim.
Acta 1993, 203, 235.
̈
1998, 1923. (f) Hirao, T.; Asahara, M.; Muguruma, Y.; Ogawa, A. J. Org.
Chem. 1998, 63, 2812. (g) Hirao, T.; Ogawa, A.; Asahara, M. Org. Synth.
2005, 81, 26. For catalytic Nozaki−Hiyama−Kishi reaction, see:
(h) Furstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 2533. (i) Furstner,
̈
̈
A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349. For catalytic Barbier-type
allylation, see: (j) Rosales, A.; Oller-Lopez Juan, L.; Justicia, J.; Gansauer,
A.; Oltra, J. E.; Cuerva, J. M. Chem. Commun. 2004, 2628. (k) Estev
E.; Justicia, J.; Bazdi, B.; Fuentes, N.; Paradas, M.; Choquesillo-Lazarte,
́
̈
́
ez, R.
D.; García-Ruiz, J. M.; Robles, R.; Gansauer, A.; Cuerva, J. M.; Oltra, J. E.
̈
(12) Theopold, K. H.; Holrnes, S. J.; Schrock, R. R. Angew. Chem., Int.
Ed. Engl. 1983, 22, 1010.
(13) Hermes, A. R.; Giriolami, G. S. Inorg. Synth. 1998, 32, 309.
́
Chem.−Eur. J. 2009, 15, 2774. (l) Justicia, J.; Sancho-Sanz, I.; Avarez-
Manzaneda, E.; Oltra, J. E.; Cuerva, J. M. Adv. Synth. Catal. 2009, 351,
2295. For catalytic Reformatsky coupling reaction, see: (m) Sgreccia, L.;
Bandini, M.; Morganti, S.; Quintavalla, A.; Umani-Ronchi, A.; Cozzi, P.
(14) Arteaga-Muller, R. A.; Tsurugi, H.; Saito, T.; Yanagawa, M.; Oda,
̈
S.; Mashima, K. J. Am. Chem. Soc. 2009, 131, 5370. (b) Tsurugi, H.;
Saito, T.; Tanahashi, H.; Arnold, J.; Mashima, K. J. Am. Chem. Soc. 2011,
133, 18673. (c) Tsurugi, H.; Tanahashi, H.; Nishiyama, H.; Fegler, W.;
Saito, T.; Sauer, A.; Okuda, J.; Mashima, K. J. Am. Chem. Soc. 2013, 135,
5986.
G. J. Organomet. Chem. 2007, 692, 3191. (n) Estev
́
ez, R. E.; Paradas, M.;
Millan, A.; Jimenez, T.; Robles, R.; Cuerva, J. M.; Oltra, J. E. J. Org. Chem.
́
́
2008, 73, 1616. For catalytic reductive cyclization of olefinic epoxide,
enone, and ketonitrile, see: (o) Kablaoui, N. M.; Buchwald, S. L. J. Am.
Chem. Soc. 1995, 117, 6785. (p) Crowe, W. E.; Rachita, M. J. J. Am.
Chem. Soc. 1995, 117, 6787. (q) Kablaoui, N. M.; Buchwald, S. L. J. Am.
(15) (a) Bock, H.; Kaim, W. Tetrahedron Lett. 1977, 27, 2343.
(b) Bock, H.; Kaim, W. J. Am. Chem. Soc. 1980, 102, 4429. (c) Kaim, W.
Angew. Chem., Int. Ed. Engl. 1981, 20, 599. (d) Kaim, W. Angew. Chem.,
Int. Ed. Engl. 1981, 20, 600. (e) Bock, H.; Kaim, W. Acc. Chem. Res. 1982,
15, 9. (f) Kaim, W. Angew. Chem., Int. Ed. Engl. 1983, 22, 171. (g) Kaim,
W. Angew. Chem., Int. Ed. Engl. 1984, 23, 613. (h) Baumgarten, J.;
Bessenbacher, C.; Kaim, W.; Stahl, T. J. Am. Chem. Soc. 1989, 111, 2126.
(i) Lichtblau, A.; Ehlend, A.; Hausen, H. D.; Kaim, W. Chem. Ber. 1995,
128, 745.
(16) Kaim, W. J. Am. Chem. Soc. 1983, 105, 707.
(17) Pattiasina, J. W.; van Bolhuis, F.; Teuben, J. H. Angew. Chem., Int.
Ed. Engl. 1987, 26, 330.
(18) Kraft, S.; Hanuschek, E.; Beckhaus, R.; Haase, D.; Saak, W.
Chem.−Eur. J. 2005, 11, 969.
(19) Enders, M.; Fink, J.; Maillant, V.; Pritzkow, H. Z. Anorg. Allg.
Chem. 2001, 627, 2281.
(20) Battaglia, L. P.; Nardelli, M.; Pelizzi, C.; Predieri, G. J. Organomet.
Chem. 1983, 259, 301.
Chem. Soc. 1996, 118, 3182. (r) Gansauer, A.; Pierobon, M.; Bluhm, H.
̈
Angew. Chem., Int. Ed. 1998, 37, 101. (s) Zhou, L.; Hirao, T. Tetrahedron
2001, 57, 6927. (t) Streuff, J.; Feurer, M.; Bichovski, P.; Frey, G.;
Gellrich, U. Angew. Chem., Int. Ed. 2012, 51, 8661.
(4) Representative references for N2 reduction: (a) Komori, K.; Oshita,
H.; Mizobe, Y.; Hidai, M. J. Am. Chem. Soc. 1989, 111, 1939. (b) Tanaka,
H.; Sasada, A.; Kouno, T.; Yuki, M.; Miyake, Y.; Nakanishi, H.;
Nishibayashi, Y.; Yoshizawa, K. J. Am. Chem. Soc. 2001, 133, 3498.
(c) Chirik, P. J.; Henling, L. M.; Bercaw, J. E. Organometallics 2001, 20,
534. (d) Yandulov, D. V.; Schrock, R. R. Science 2003, 301, 76.
(e) Bradley, C. A.; Veiros, L. F.; Pun, D.; Lobkovsky, E.; Keresztes, I.;
Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 16600. (f) Hirotsu, M.;
Fontaine, P. P.; Epshteyn, A.; Zavalij, P. Y.; Sita, L. R. J. Am. Chem. Soc.
2007, 129, 9284. (g) Pun, D.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem.
Soc. 2008, 130, 6047. (h) Pun, D.; Bradley, C. A.; Lobkovsky, E.;
Keresztes, I.; Chirik, P. J. J. Am. Chem. Soc. 2008, 130, 14046.
(i) Knobloch, D. J.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2010,
132, 10553. (j) Knobloch, D. J.; Lobkovsky, E.; Chirik, P. J. Nat. Chem.
2010, 2, 30. (k) Fontaine, P. P.; Yonke, B. L.; Zavalij, P. Y.; Sita, L. R. J.
Am. Chem. Soc. 2010, 132, 12273. (l) Arashiba, K.; Miyake, Y.;
Nishibayashi, Y. Nat. Chem. 2011, 3, 120. (m) Tanaka, H.; Sasada, A.;
Kouno, T.; Yuki, M.; Miyake, Y.; Nakanishi, H.; Nishibayashi, Y.;
Yoshizawa, K. J. Am. Chem. Soc. 2011, 133, 3498. (n) Semproni, S. P.;
Milsmann, C.; Chirik, P. J. Organometallics 2012, 31, 3672.
(o) Semproni, S. P.; Knobloch, D. J.; Milsmann, C.; Chirik, P. J.
Angew. Chem., Int. Ed. 2013, 52, 5372.
(5) Representative references for CO activation: (a) Watanabe, T.;
Ishida, Y.; Matsuo, T.; Kawaguchi, H. J. Am. Chem. Soc. 2009, 131, 3474.
(b) Reeds, J. P.; Yonke, B. L.; Zavalij, P. Y.; Sita, L. R. J. Am. Chem. Soc.
2011, 133, 18602.
(6) Representative references for CO2 activation: (a) Bryan, J. C.;
Geib, S. J.; Rheingold, A. L.; Mayer, J. M. J. Am. Chem. Soc. 1987, 109,
2826. (b) Hall, K. A.; Mayer, J. M. J. Am. Chem. Soc. 1992, 114, 10402.
(c) Yonke, B. L.; Reeds, J. P.; Zavalij, P. Y.; Sita, L. R. Angew. Chem., Int.
Ed. 2011, 50, 12342.
(7) Representative references for activation of multiple bonds:
(a) Schrock, R. R.; Listemann, M. L.; Sturgeoff, L. G. J. Am. Chem.
Soc. 1982, 104, 4291. (b) Bryan, J. C.; Mayer, J. M. J. Am. Chem. Soc.
1987, 109, 7213. (c) Bryan, J. C.; Mayer, J. M. J. Am. Chem. Soc. 1990,
112, 2298. (d) Bryan, J. C.; Arterburn, J. B.; Cook, G. K.; Mayer, J. M.
Organometallics 1992, 11, 3965. (e) Tsai, Y.-C.; Johnson, M. J. A.;
Mindiola, D. J.; Cummins, C. C. J. Am. Chem. Soc. 1999, 121, 10426.
(f) Sattler, A.; Parkin, G. Nature 2010, 463, 523.
(8) Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877.
(9) (a) Sekutowski, D. J.; Stucky, G. D. Inorg. Chem. 1975, 14, 2192.
(b) Enemærke, R. J.; Larsen, J.; Skrydstrup, T.; Daasbjerg, K.
Organometallics 2004, 23, 1866. (c) Enemærke, R. J.; Larsen, J.;
Skrydstrup, T.; Daasbjerg, K. J. Am. Chem. Soc. 2004, 126, 7853.
(21) Langmaier, J.; Samec, Z.; Varga, V.; Horac
Organomet. Chem. 1999, 579, 348.
́ ̌
ek, M.; Mach, K. J.
(22) Nieman, J.; Pattiasina, J. W.; Teuben, J. H. J. Organomet. Chem.
1984, 262, 157.
(23) (a) Schofield, A. D.; Nova, A.; Selby, J. D.; Schwarz, A. D.; Clot,
E.; Mountford, P. Chem.−Eur. J. 2011, 17, 265. (b) Tran, B. L.;
Washington, M. P.; Henckel, D. A.; Gao, X.; Park, H.; Pink, M.;
Mindiola, D. J. Chem. Commun. 2012, 48, 1529. (c) Unruangsri, J.;
Morgan, H.; Schwarz, A. D.; Schofield, A. D.; Mountford, P.
Organometallics 2013, 32, 3091.
(24) Hausen, H. D.; Mundt, H.; Kaim, W. J. Organomet. Chem. 1985,
296, 321.
(25) Mashima, K.; Matsuo, Y.; Tani, K. Organometallics 1999, 18, 1471.
(26) Ting, C.; Messerle, L. Inorg. Chem. 1989, 28, 173.
(27) Rothfuss, H.; Barry, J. T.; Huffman, J. C.; Caulton, K. G.;
Chisholm, M. H. Inorg. Chem. 1993, 32, 4573.
(28) (a) Kaim, W. J. Mol. Struct. (Theochem) 1984, 109, 277. (b) Vlce
P.; Havlas, Z.; Pavlícek, Z. Collect. Czech. Chem. Commun. 1999, 64, 633.
(29) Computational results are summarized in SI.
̌
k,
̌
(30) Huang, K.-W.; Waymouth, R. M. J. Am. Chem. Soc. 2002, 124,
8200.
(31) Reactions of organosilicon compounds 2a,b and 4 with ethyl 2-
bromoisobutyrate are described in SI.
(32) Ehlend, A.; Hausen, H. D.; Kaim, W.; Lichtblau, A.; Schwarz, W. J.
Organomet. Chem. 1995, 501, 283.
(33) Scope and limitation of the Reformatsky reaction catalyzed by
Cp2TiCl2/2c is described in SI.
(34) (a) Weyenberg, D. R.; Toporcer, L. H. J. Am. Chem. Soc. 1962, 84,
2843. (b) Laguerre, M.; Dunogues, J.; Calas, R.; Duffaut, N. J.
Organomet. Chem. 1976, 112, 49.
(35) Gorsich, R. D. J. Am. Chem. Soc. 1958, 80, 4744.
I
dx.doi.org/10.1021/ja501313s | J. Am. Chem. Soc. XXXX, XXX, XXX−XXX