Organometallics
Article
The authors thank William C. Ewing for valuable comments on
the manuscript. Dedicated to Prof. Todd B. Marder on the
occasion of his 60th birthday.
164−167. (c) Stone, F. G. A. Inorg. Chim. Acta 1981, 50, 33−42.
(d) King, R. B.; Kapoor, P. N. Inorg. Chem. 1972, 11, 1524−1527.
(
10) (a) Bo
Herrmann, W. A. J. Organomet. Chem. 2000, 595, 186−190.
b) Caddick, S.; Cloke, F. G. N.; Clentsmith, G. K. B.; Hitchcock,
̈ ̈
hm, V. P. W.; Gstottmayr, C. W. K.; Weskamp, T.;
(
REFERENCES
P. B.; McKerrecher, D.; Titcomb, L. R.; Williams, M. R. V. J.
Organomet. Chem. 2001, 617−618, 635−639. (c) Titcomb, L. R.;
Caddick, S.; Cloke, F. G. N.; Wilson, D. J.; McKerrecher, D. Chem.
Commun. 2001, 1388−1389. (d) Arentsen, K.; Caddick, S.; Cloke, F.
G. N.; Herring, A. P.; Hitchcock, P. B. Tetrahedron Lett. 2004, 45,
■
(
1) (a) Hartwig, J. Organotransition Metal Chemistry − from Bonding
to Catalysis; University Science Books: Sausalito, 2010. (b) Elschen-
broich, C. Organometallics, 3rd ed.; Weinheim, 2006. (c) Crabtree, R.
H. The Organometallic Chemistry of the Transition Metals, 4th ed.;
Wiley: Hoboken, 2005. (d) Cornils, B.; Herrmann, W. A., Eds. Applied
Homogeneous Catalysis with Organometallic Compounds, 2nd ed.;
Weinheim, 2002. (e) Steinborn, D. Grundlagen der Metallorganischen
Komplexkatalyse, 2nd ed.; Vieweg + Teubner: Wiesbaden, 2010.
3
511−3515. (e) Gsto
E.; Grosche, M.; Herrmann, W. A. Angew. Chem. 2002, 114, 1421−
423; Angew. Chem., Int. Ed. 2002, 41, 1363−1365. (f) Altenhoff, G.;
Goddard, R.; Lehmann, C. W.; Glorius, F. Angew. Chem. 2003, 115,
818−3821; Angew. Chem., Int. Ed. 2003, 42, 3690−3693. (g) Konnick,
M. M.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126, 10212−
0213. (h) Yamashita, M.; Goto, K.; Kawashima, T. J. Am. Chem. Soc.
̈ ̈
ttmayr, C. W. K.; Bohm, V. P. W.; Herdtweck,
1
3
(2) Ugo, R. Coord. Chem. Rev. 1968, 3, 319−344.
(3) (a) Murai, S., Ed. Activation of Unreactive Bonds and Organic
1
Synthesis. In Topics in Organometallic Chemistry; Springer: Berlin,
999. (b) Kubas, G. J. Metal Dihydrogen and Sigma-Bond Complexes;
1
2005, 127, 7294−7295. (i) Fantasia, S.; Nolan, S. P. Chem.Eur. J.
2008, 14, 6987−6993. (j) Lee, E.; Yandulov, D. V. J. Organomet. Chem.
2011, 696, 4095−4103.
Kluwer Academic/Plenum Publishers: New York, 2001. (c) Goldman,
A. S.; Goldberg, K. I., Eds. Activation and Functionalization of C-H
Bonds, ACS Symposium Series 885; ACS: Washington, DC, 2004.
(11) Matsumoto, M.; Yoshioko, H.; Nakatsu, K.; Yoshida, T.; Otsuka,
S. J. Am. Chem. Soc. 1974, 96, 3322−3324.
(
2
d) Perutz, R. N.; Sabo-Etienne, S. Angew. Chem. 2007, 119, 2630−
(12) (a) Arduengo, A. J.; Gamper, S. F.; Calabrese, J. C.; Davidson, F.
645; Angew. Chem., Int. Ed. 2007, 46, 2578−2592. (e) Corey, J. Y.;
Braddock-Wilking, J. Chem. Rev. 1999, 99, 175−292. (f) Corey, J. Y.
J. Am. Chem. Soc. 1994, 116, 4391−4394. (b) Arnold, P. L.; Cloke, F.
G. N.; Geldbach, T.; Hitchcock, P. B. Organometallics 1999, 18, 3228−
3233. (c) Fortman, G. C.; Scott, N. M.; Linden, A.; Stevens, E. D.;
Dorta, R.; Nolan, S. P. Chem. Commun. 2010, 46, 1050−1052.
(d) Bauer, J.; Braunschweig, H.; Brenner, P.; Kraft, K.; Radacki, K.;
Schwab, K. Chem.Eur. J. 2010, 16, 11985−11992.
Chem. Rev. 2011, 111, 863−1071. (g) Marciniec, B., Ed. Hydrosilylation
-
(
A Comprehensive Review on Recent Advances; Springer: Houten, 2009.
h) Frisch, A. C.; Beller, M. Angew. Chem. 2005, 117, 680−695; Angew.
Chem., Int. Ed. 2005, 44, 674−688. (i) Corbet, J.-P.; Mignani, G. Chem.
Rev. 2006, 106, 2651−2710. (j) Molander, G. A.; Canturk, B. Angew.
Chem. 2009, 121, 9404−9425; Angew. Chem., Int. Ed. 2009, 48, 9240−
(13) (a) McGuinness, D. S.; Cavell, K. J.; Skelton, B. W.; White, A.
H. Organometallics 1999, 18, 1596−1605. (b) Clement, N. D.; Cavell,
K. J.; Ooi, L.-l. Organometallics 2006, 25, 4155−4165.
9
(
261. (k) Amii, H.; Uneyama, K. Chem. Rev. 2009, 109, 2119−2183.
l) Clot, E.; Eisenstein, O.; Jasim, N.; MacGregor, S. A.; McGrady, J.
E.; Perutz, R. N. Acc. Chem. Res. 2011, 44, 333−348.
4) (a) Malatesta, L.; Angoletta, M. J. Chem. Soc. 1957, 1186−1188.
b) Malatesta, L.; Cariello, C. J. Chem. Soc. 1958, 2323−2328. (c) Ugo,
R.; Cariati, F.; La Monica, G. Chem. Commun. 1966, 868−869.
d) Fitton, P.; McKeon, J. E. Chem. Commun. 1968, 4−6. (e) Immirzi,
(14) For the reaction of NHCs with activated C−C double bonds
such as in dba, see: (a) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.;
Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem. 1995, 107,
1119−1122; Angew. Chem., Int. Ed. Engl. 1995, 34, 1021−1023.
(b) Enders, D.; Breuer, K.; Runsink, J.; Henrique Teles, J. Liebigs Ann.
Chem. 1996, 1996, 2019−2028. (c) Braun, M.; Frank, W.; Ganter, C.
Organometallics 2012, 31, 1927−1934.
(
(
(
A.; Musco, A.; Zambelli, P.; Carturan, G. Inorg. Chim. Acta 1975, 13,
L13−L14. (f) Otsuka, S.; Yoshida, T.; Matsumoto, M.; Nakatsu, K. J.
Am. Chem. Soc. 1976, 98, 5850−5858. (g) Yoshida, T.; Otsuka, S.
Inorg. Synth. 1979, 19, 101−107. (h) Moynihan, K. J.; Chieh, C.; Goel,
R. G. Acta Crystallogr., Sect. B 1979, B35, 3060−3062.
(15) (a) Cook, C. D.; Jauhal, G. S. Inorg. Nucl. Chem. Lett. 1967, 3,
31−33. (b) Tolman, C. A.; Seidel, W. C.; Gerlach, D. H. J. Am. Chem.
Soc. 1972, 94, 2669−2676. (c) Blake, D. M.; Roundhill, D. M. Inorg.
Synth. 1978, 18, 120−124. (d) Head, R. A. Inorg. Synth. 1986, 24,
213−216. (e) Head, R. A. Inorg. Synth. 1990, 28, 132−135. (f) Nagel,
U. Chem. Ber. 1982, 115, 1998−1999.
(16) Drew, D.; Doyle, J. R. Inorg. Synth. 1990, 28, 346−349.
(17) Clement, N. D.; Cavell, K. J.; Jones, C.; Elsevier, C. J. Angew.
Chem. 2004, 116, 1297−1299; Angew. Chem., Int. Ed. 2004, 42,
1277−1279
(18) (a) Burling, S.; Mahon, M. F.; Powell, R. E.; Whittlesey, M. K.;
Williams, J. M. J. J. Am. Chem. Soc. 2006, 128, 13702−13703.
(b) Haller, L. J. L.; Page, M. J.; Erhardt, S.; MacGregor, S. A.; Mahon,
M. F.; Naser, M. A.; Velez, A.; Whittlesey, M. K. J. Am. Chem. Soc.
2010, 132, 18408−18416.
(19) Kaufhold, O.; Stasch, A.; Pape, T.; Hepp, A.; Edwards, P. G.;
Newman, P. D.; Hahn, F. E. J. Am. Chem. Soc. 2009, 131, 306−317.
(20) (a) Huertos, M. A.; Perez, J.; Riera, L.; Menendez-Velazquez, A.
J. Am. Chem. Soc. 2008, 130, 13530−13531. (b) Araki, K.; Kuwata, S.;
Ikariya, T. Organometallics 2008, 27, 2176−2178. (c) Miranda-Soto,
V.; Grotjahn, D. B.; DiPasquale, A. G.; Rheingold, A. L. J. Am. Chem.
(
5) See for example: (a) Lappert, M. F.; Sanger, A. R. J. Chem. Soc. A
1
971, 1314−1320. (b) Otsuka, S.; Yoshida, T.; Matsumoto, M.;
Nakatsu, K. J. Am. Chem. Soc. 1976, 98, 5850−5858. (c) Immirzi, A.;
Musco, A.; Zambelli, P.; Carturan, G. Inorg. Chim. Acta 1975, 13,
L13−L14. (d) Moynihan, K. J.; Chieh, C.; Goel, R. G. Acta Crystallogr.,
Sect. B 1979, B35, 3060−3062. (e) Yoshida, T.; Otsuka, S. Inorg. Synth.
1
979, 19, 101−107. (f) Braunschweig, H.; Brenner, P.; Dewhurst, R.
D.; Guethlein, F.; Jimenez-Halla, J. O. C.; Radacki, K.; Wolf, J.;
Zo
llner, L. Chem.Eur. J. 2012, 18, 8605−8609.
6) (a) Bauer, J.; Braunschweig, H.; Dewhurst, R. D. Chem. Rev.
̈
(
2
012, 112, 4329−4346. (b) Braunschweig, H.; Dewhurst, R. D.;
Gessner, V. H. Chem. Soc. Rev. 2013, 42, 3197−3208. (c) Brand, J.;
Braunschweig, H.; Sen, S. S. Acc. Chem. Res. 2014, 47, 180−191.
(
Angew. Chem., Int. Ed. 2002, 41, 1290−1309. (b) Nolan, S. P., Ed. N-
Heterocyclic Carbenes in Synthesis; Wiley-VCH: Weinheim, 2006.
7) (a) Herrmann, W. A. Angew. Chem. 2002, 114, 1342−1363;
(
c) Glorius, F., Ed. N-Heterocyclic Carbenes in Transition Metal
Catalysis. In Topics in Organometallic Chemistry, Vol. 21; Springer:
Berlin, 2007. (d) Jahnke, M. C.; Hahn, F. E. Angew. Chem. 2008, 120,
Soc. 2008, 130, 13200−13201. (d) Huertos, M. A.; Per
́
ez, J.; Riera, L.;
3
166−3216; Angew. Chem., Int. Ed. 2008, 47, 3122−3172. (e) Diez-
Gonzalez, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612−
676. (f) Droge, T.; Glorius, F. Angew. Chem. 2010, 122, 7094−7107;
Angew. Chem., Int. Ed. 2010, 49, 6940−6952.
8) Hering, F.; Nitsch, J.; Paul, U.; Steffen, A.; Bickelhaupt, F. M.;
Radius, U. Chem. Sci. 2015, 6, 1426−1432.
9) (a) Malatesta, L.; Ugo, R.; Cenini, S. Adv. Chem. Ser. 1967, 62,
18−356. (b) Rosevear, D. T.; Stone, F. G. A. J. Chem. Soc. 1968,
Díaz, J.; Lopez, R. Angew. Chem. 2010, 122, 6553−6556; Angew.
́
Chem., Int. Ed. 2010, 49, 6409−6412. (e) Huertos, M. A.; Perez, J.;
Riera, L.; Diaz, J.; Lopez, R. Chem.Eur. J. 2010, 16, 8495−8507.
(f) Miranda-Soto, V.; Grotjahn, D. B.; Cooksy, A. L.; Golen, J. A.;
Moore, C. E.; Rheingold, A. L. Angew. Chem. 2011, 123, 657−661;
Angew. Chem., Int. Ed. 2011, 50, 631−635. (g) Brill, M.; Diaz, J.;
Huertos, M. A.; Lopez, R.; Perez, J.; Riera, L. Chem.Eur. J. 2011, 17,
3
̈
(
(
3
̈ ̈
̈ ̈
8584−8595. (h) Kosterke, T.; Kosters, J.; Wurthwein, E.-U.; Muck-
3
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Organometallics 2015, 34, 3236−3245