Inorganic Chemistry
Article
(
3) (a) Messerle, L.; Curtis, M. D. J. Am. Chem. Soc. 1980, 102,
(17) Tilley, T. D.; Grubbs, R. H.; Bercaw, J. E. Organometallics 1984,
3, 274−278.
(18) Boren, B. C.; Narayan, S.; Rasmussen, L. K.; Zhang, L.; Zhao,
H.; Lin, Z.; Jia, G.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 8923−
8930.
7
789−7791. (b) Woodcock, C.; Eisenberg, R. Organometallics 1985, 4,
4−7. (c) Curtis, M. D.; Messerle, L.; D’Errico, J. J.; Butler, W. M.; Hay,
M. S. Organometallics 1986, 5, 2283−2294.
(
4) (a) Nakamura, A.; Yoshida, T.; Cowie, M.; Otsuka, S.; Ibers, J. A.
J. Am. Chem. Soc. 1977, 99, 2108−2117. (b) Schramm, K. D.; Ibers, J.
A. Inorg. Chem. 1980, 19, 1231−1236. (c) Schramm, K. D.; Ibers, J. A.
Inorg. Chem. 1980, 19, 2435−2440. (d) Schramm, K. D.; Ibers, J. A.
Inorg. Chem. 1980, 19, 2441−2448. (e) Hillhouse, G. L.; Haymore, B.
L. J. Am. Chem. Soc. 1982, 104, 1537−1548. (f) Cowie, M.; Loeb, S. J.;
McKeer, I. R. Organometallics 1986, 5, 854−865. (g) Kaplan, A. W.;
Polse, J. L.; Ball, G. E.; Andersen, R. A.; Bergman, R. G. J. Am. Chem.
Soc. 1998, 120, 11649−11662. (h) Kwen, H.; Young, V. G., Jr.; Maatta,
E. A. Angew. Chem., Int. Ed. 1999, 38, 1145−1146. (i) Dias, E. L.;
Brookhart, M.; White, P. S. J. Am. Chem. Soc. 2001, 123, 2442−2443.
(19) APEX2, SMART, SAINT; Bruker AXS Inc.: Madison, WI, USA,
2007.
(20) McArdle, P. J. Appl. Crystallogr. 1995, 28, 65−65.
(21) Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr.
2008, 64, 112−122.
(22) Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Adv. 2015, 71,
3−8.
(23) Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, 71,
3−8.
(24) (a) Minenkov, Y.; Singstad, Å.; Occhipinti, G.; Jensen, V. R.
Dalton Trans. 2012, 41, 5526−5541. (b) Chai, J.-D.; Head-Gordon, M.
Phys. Chem. Chem. Phys. 2008, 10, 6615−6620. (c) Gerber, I. C.;
(
j) Werner, H.; Mahr, N.; Wolf, J.; Fries, A.; Laubender, M.; Bleuel, E.;
Garde, R.; Lahuerta, P. Organometallics 2003, 22, 3566−3576.
5) (a) Ben-Shoshan, R.; Chatt, J.; Leigh, G. J.; Hussain, W. J. Chem.
(
́
Angyan
25) (a) Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7,
297−3305. (b) Andrae, D.; Haussermann, U.; Dolg, M.; Stoll, H.;
Preuss, H. Theor. Chim. Acta 1990, 77, 123−141.
26) Cramer, C. J. Essentials of Computational Chemistry, 2nd Ed.;
Wiley: Chichester, UK, 2004.
27) (a) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput.
Chem. 2003, 24, 669−681. (b) Barone, V.; Cossi, M. J. Phys. Chem. A
998, 102, 1995−2001.
28) Frisch, M. J. et al. Gaussian 09, Revision C.01; Gaussian Inc.,
Wallingford, CT, USA, 2010.
́
, J. G. Chem. Phys. Lett. 2005, 415, 100−105.
Soc., Dalton Trans. 1980, 771−775. (b) Hidai, M.; Aramaki, S.;
Yoshida, K.; Kodama, T.; Takahashi, T.; Uchida, Y.; Mizobe, Y. J. Am.
Chem. Soc. 1986, 108, 1562−1568.
(
3
̈
(
6) (a) Albertin, G.; Antoniutti, S.; Baldan, D.; Castro, J.; Comparin,
(
G. Organometallics 2013, 32, 3157−3160. (b) Albertin, G.; Antoniutti,
S.; Botter, A.; Castro, J.; Giacomello, M. Organometallics 2014, 33,
(
3
570−3582. (c) Albertin, G.; Antoniutti, S.; Callegaro, F.; Castro, J.
Organometallics 2009, 28, 4475−4479. (d) Albertin, G.; Antoniutti, S.;
1
Bordignon, E.; Carrera, B. Inorg. Chem. 2000, 39, 4646−4650.
(
(
7) (a) Sutton, D. Chem. Rev. 1993, 93, 995−1022. (b) Hidai, M.;
Mizobe, Y. Chem. Rev. 1995, 95, 1115−1133.
(
(29) Geary, W. J. Coord. Chem. Rev. 1971, 7, 81−172.
(30) Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565−565.
(31) McCarty, W. J.; Yang, X.; DePue Anderson, L. J. D.; Jones, R. A.
8) (a) Kisch, H.; Holzmeier, P. Adv. Organomet. Chem. 1992, 34,
67−109. (b) Sellmann, D. Angew. Chem., Int. Ed. Engl. 1993, 32, 64−
67. (c) Zollinger, H. Diazo Chemistry II; VCH: Weinheim, Germany,
1995.
Dalton Trans. 2012, 41, 13496−13503.
32) Albertin, G.; Antoniutti, S.; Bortoluzzi, M.; Castro, J.; Marzaro,
L. Dalton Trans. 2015, 44, 15470−15480.
33) Albertin, G.; Antoniutti, S.; Castro, J.; Dottorello, G. Dalton
Trans. 2015, 44, 9289−9303.
34) Patai, S. The Chemistry of Diazonium and Diazo Groups; Wiley &
Sons: Chichester, UK, 1978.
35) McGarrity, J. F.; Smyth, T. J. Am. Chem. Soc. 1980, 102, 7303−
308.
36) Wiberg, N.; Bachhuber, H.; Fischer, G. Angew. Chem., Int. Ed.
Engl. 1972, 11, 829−830.
37) (a) Corey, E. J.; Pasto, D. J.; Mock, W. L. J. Am. Chem. Soc.
961, 83, 2957−2958. (b) van Tamelen, E. E.; Timmons, R. J. J. Am.
Chem. Soc. 1962, 84, 1067−1068.
38) (a) Barney, B. M.; McClead, J.; Lukoyanov, D.; Laryukhin, M.;
Yang, T.-C.; Dean, D. R.; Hoffman, B. M.; Seefeldt, L. C. Biochemistry
(
(
9) (a) Baratta, W.; Del Zotto, A.; Rigo, P. Organometallics 1999, 18,
5
091−5096. (b) Del Zotto, A.; Baratta, W.; Sandri, M.; Verardo, G.;
(
Rigo, P. Eur. J. Inorg. Chem. 2004, 2004, 524−529. (c) Seino, H.;
Watanabe, D.; Ohnishi, T.; Arita, C.; Mizobe, Y. Inorg. Chem. 2007, 46,
(
4
2
784−4786. (d) Zarkesh, R. A.; Heyduk, A. F. Organometallics 2009,
8, 6629−6631. (e) Alvarez, M. A.; García, M. E.; Gonzalez, R.; Ruiz,
(
7
(
M. A. Organometallics 2010, 29, 5140−5153. (f) Ren, W.; Zhou, E.;
Fang, B.; Hou, G.; Zi, G.; Fang, D.-C.; Walter, M. D. Angew. Chem., Int.
Ed. 2014, 53, 11310−11314.
(
10) (a) Herrmann, W. A. Angew. Chem., Int. Ed. Engl. 1978, 17,
(
1
8
00−812. (b) Doyle, M. P. Chem. Rev. 1986, 86, 919−939. (c) Roper,
W. R. J. Organomet. Chem. 1986, 300, 167−190. (d) Putala, M.;
Lemenovskii, D. A. Russ. Chem. Rev. 1994, 63, 197−216. (e) Werner,
H. J. Organomet. Chem. 1995, 500, 331−336. (f) Che, C.-M.; Huang,
J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-
S.; Lo, W.-C.; Peng, S.-M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123,
(
2
007, 46, 6784−6794. (b) Coucouvanis, D. Acc. Chem. Res. 1991, 24,
1
−8. (c) Back, R. A. Rev. Chem. Intermed. 1984, 5, 293−323.
4
2
4
1
119−4129. (g) Mindiola, D. J.; Hillhouse, G. L. J. Am. Chem. Soc.
002, 124, 9976−9977. (h) Kirmse, W. Angew. Chem., Int. Ed. 2003,
2, 1088−1093. (i) Dai, X.; Warren, T. H. J. Am. Chem. Soc. 2004, 126,
0085−10094. (j) Shishkov, I. V.; Rominger, F.; Hofmann, P.
(
d) Thorneley, R. N. F.; Eady, R. R.; Lowe, D. J. Nature 1978, 272,
5
(
57−558.
39) (a) Sellmann, D.; Hille, A.; Rosler, A.; Heinemann, F. W.; Moll,
M.; Brehm, G.; Schneider, S.; Reiher, M.; Hess, B. A.; Bauer, W. Chem.
pler, J.; Moll, M.;
Organometallics 2009, 28, 1049−1059. (k) Egloff, J.; Ranocchiari,
M.; Schira, A.; Schotes, C.; Mezzetti, A. Organometallics 2013, 32,
-
Eur. J. 2004, 10, 819−830. (b) Sellmann, D.; Kap
̈
Knoch, F. Inorg. Chem. 1993, 32, 960−964. (c) Fujisawa, K.; Lehnert,
4
690−4701. (l) Kornecki, K. P.; Briones, J. F.; Boyarskikh, V.;
N.; Ishikawa, Y.; Okamoto, K. Angew. Chem., Int. Ed. 2004, 43, 4944−
Fullilove, F.; Autschbach, J.; Schrote, K. E.; Lancaster, K. M.; Davies,
4
947.
H. M. L.; Berry, J. F. Science 2013, 342, 351−354.
(40) (a) Cheng, T.-Y.; Ponce, A.; Rheingold, A. L.; Hillhouse, G. L.
(
11) Albertin, G.; Antoniutti, S.; Botter, A.; Castro, J. Inorg. Chem.
Angew. Chem., Int. Ed. Engl. 1994, 33, 657−659. (b) Smith, M. R., III;
Cheng, T.-Y.; Hillhouse, G. L. J. Am. Chem. Soc. 1993, 115, 8638−
8642. (c) Zhang, Q.-F.; Zheng, H.; Wong, W.-Y.; Wong, W.-T.; Leung,
W.-H. Inorg. Chem. 2000, 39, 5255−5264.
(41) (a) Field, L. D.; Li, H. L.; Dalgarno, S. J. Inorg. Chem. 2010, 49,
6214−6221. and references therein. (b) Field, L. D.; Li, H. L.;
Dalgarno, S. J.; Turner, P. Chem. Commun. 2008, 1680−1682.
(42) Previous reports (see ref 41) suggest a more probable trans
diazene isomer, and the most populated electronic density around the
nitrogen atoms found in 7 fits a trans disposition.
2
(
(
015, 54, 2091−2093.
12) Rabinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623−4626.
13) (a) Smith, L. I.; Howard, K. L. Organic Syntheses; Wiley: New
York, 1955; Vol. III, p 351. (b) Miller, J. B. J. Org. Chem. 1959, 24,
60−561. (c) Baltzly, R.; Mehta, N. B.; Russell, P. B.; Brooks, R. E.;
5
(
(
15) Gerlach, M.; Putz, C.; Enders, D.; Gaube, G. Patent No. WO
0
(
2/22569, 2002.
16) Searle, N. E. Organic Syntheses, Coll. 1963, 4, 424.
J
Inorg. Chem. XXXX, XXX, XXX−XXX