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http://dx.doi.org/10.1246/cl.******.
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2002, 35, 2455. h) N. Agenet, J.-H. Mirebeau, M. Petit, R.
Thouvenot, V. Gandon, M. Malacria, C. Aubert,
Organometallics 2007, 26, 819. i) K. Hirano, H. Yorimitsu, K.
Oshima, J. Am. Chem. Soc. 2007, 129, 6094. j) S. Saito, T.
Yoshizawa, S. Ishigami, R. Yamasaki, Tetrahedron Lett. 2010,
51, 6028.
N-Heterocyclic carbenes alone promote a variety of reactions
incorporating carbon dioxide, see: a) H. Zhou, W.-Z. Zhang, C.-
H. Liu, J.-P. Qu, X.-B. Lu, J. Org. Chem. 2008, 73, 8039. b) S. N.
Riduan, Y. Zhang, J. Y. Ying, Angew. Chem. Int. Ed. 2009, 48,
3322. c) I. Tommasi, F. Sorrentino, Tetrahedron Lett. 2009, 50,
104. d) Y. Kayaki, M. Yamamoto, T. Ikariya, Angew. Chem. Int.
Ed. 2009, 48, 4194. e) L. Gu, Y. Zhang, J. Am. Chem. Soc. 2010,
132, 914. f) J. Seayad, A. M. Seayad, J. K. P. Ng, C. L. L. Chai,
ChemCatChem 2012, 4, 774. g) O. Jacquet, C. D. N. Gomes, M.
Ephrtikhine, T. Cantat, J. Am. Chem. Soc. 2012, 134, 2934. h) F.
D. Bobbink, W. Gruszka, M. Hulla, S. Das, P. J. Dyson, Chem.
Commun. 2016, 52, 10787. i) F. D. Bobbink, S. Das, P. J. Dyson,
Nat. Protocol 2017, 12, 417.
For a review on N-heterocyclic carbene-mediated activation of
organosilicon compounds: M. J. Fuchter, Chem. Eur. J. 2010, 16,
12286.
Aresta, M.; Nobile, C. F.; Albano, V. G.; Forni, E.; Manassero,
M. J. Chem. Soc., Chem. Commun. 1975, 15, 636.
Sadighi reported a nickel(0) complex having an IPr ligand reacts
with carbon dioxide to form a unique dinuclear nickel complex
bridged with CO and CO . C. H. Lee, D. S. Laitar, P. Mueller, J.
2
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7
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7
7
7
7
7
8
8
8
8
8
8
8
8
8
8
9
9
9
9
9
9
9
9
9
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
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9
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References and Notes
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5
6
7
8
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1
2
3
4
5
6
7
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1
2
3
M. Melaimi, L. Ricard, F. Mathey, P. Le Floch, Org. Lett. 2002,
4, 1245.
G. I. McGrew, P. A. Khatir, W. E. Geiger, R. A. Kemp, R.
Waterman, Chem. Commun. 2015, 51, 15804.
N. Nakata, R. Rodiguez, T. Troadec, N. Saffon-Merceron, J.-M.
Sotiropoulos, A. Baceiredo, T. Kato, Angew. Chem. Int. Ed. 2013,
52, 10840.
12
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
3
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3
3
3
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4
4
4
4
4
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4
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4
4
5
5
5
5
5
5
5
5
5
5
6
6
6
6
6
6
6
6
6
4
M. F. S. Varverde, E. Theuergarten, T. Bannenberg, M. Freytag,
P. G. Jones, M. Tamm, Dalton Trans. 2015, 44, 9400.
5
6
T. Hattori, Y. Suzuki, S. Miyano, Chem. Lett. 2003, 32, 454.
a) Effenberger, F.; Spiegler, W. Chem. Ber. 1985, 118, 3900. b)
M. Ohno, H. Tanaka, M. Komatsu, Y. Ohshiro, Synlett 1991, 919.
c) Singh, R. P.; Shreeve, J. M. Chem. Commun. 2002, 38, 1818.
d) T. Mita, K. Michigami, Y. Sato, Org. Lett. 2012, 14, 3462. e)
M. Yonemoto-Kobayashi, K. Inamoto, Y. Tanaka, Y. Kondo,
Org. Biomol. Chem. 2013, 11, 3773. f) T. Mita, K. Michigami, Y.
Sato, Org. Lett. 2014, 16, 14. g) T. Mita, M. Sugawara, K. Saito,
Y. Sato, Org. Lett. 2014, 16, 3028. h) T. Mita, H. Tanaka, K.
Michigami, Y. Sato, Synlett 2015, 25, 1291. See also: i) Yoshida,
H.; Fukushima, H.; Ohshita, J.; Kunai, A. J. Am. Chem. Soc.
2006, 128, 11040.
13
14
15
7
8
K. Sekine, Y. Sadamitsu, T. Yamada, Org. Lett. 2015, 17, 5706.
T. V. Q. Nguyen, J. A. Rodriguez-Santamaria, W.-J. Yoo, S.
Kobayashi, Green Chem. 2017, 19, 2501. See also: Yoo, W.-J.;
Nguyen, T. V. Q.; Kobayashi, S. Angew. Chem., Int. Ed. 2014,
53, 10213.
P. Sadighi, J. Am. Chem. Soc. 2007, 129, 13802.
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Alternative reaction pathways are also conceivable. For example,
2
a pathway through 1) oxidative addition of the C(sp )–Si linkage
of 1a onto nickel(0) to form a five-membered nickelacycle
9
Selected examples of nickel-catalyzed incorporation reactions of
carbon dioxide into organic molecules: a) Y. Inoue, Y. Itoh, H.
Hashimoto, Chem. Lett. 1977, 6, 855. b) A. Behr, R. He, K.-D.
Juszaki, C. Krüger, Y.-H. Tsay, Chem. Ber. 1986, 119, 911. c) H.
Hoberg, S. Gross, A. Milchereit, Angew. Chem. Int. Ed. 1987, 26,
571. d) T. Tsuda, S. Morikawa, R. Sumiya, T. Saegusa, J. Org.
Chem. 1988, 53, 3140. e) M. Takimoto, M. Mori, J. Am. Chem.
Soc. 2002, 124, 10008. f) J. Louie, J. E. Gibby, M. V. Farnworth,
T. N. Tekavec, J. Am. Chem. Soc. 2002, 124, 15188. g) H. Ochiai,
M. Jang, K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2008,
10, 2681. h) C. S. Yeung, V. M. Dong, J. Am. Chem. Soc. 2008,
130, 7826. i) C. M. Williams, J. B. Johnson, T. Rovis, J. Am.
Chem. Soc. 2008, 130, 14936. j) S. Li, W. Yuan, S. Ma, Angew.
Chem. Int. Ed. 2011, 50, 2578. k) T. Fujihara, K. Nogi, T. Xu, J.
Terao, Y. Tsuji, J. Am. Chem. Soc. 2012, 134, 9106. l) Y. Mori,
T. Mori, G. Onodera, M. Kimura, Synthesis 2014, 46, 2287. m) Y.
Makida, E. Marelli, A. M. Z. Slawin, S. P. Nolan, Chem.
Commun. 2014, 50, 8010. n) F. Juliá-Hernández, T. Moragas, J.
Cornella, R. Martin, Nature 2017, 545, 84. o) Q.-Y. Meng, S.
Wang, B. König, Angew. Chem. Int. Ed. 2017, 56, 13426, and
references cited therein.
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intermediate, 2) insertion of carbon dioxide into the resulting
2
C(sp )–Ni bond to furnish a seven-membered nickelalactone, and
3) O–Si bond forming reductive elimination leads to the
formation of 3a.
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Reactions of silacyclobutenes with carbonyl compounds: a) P. B.
Valkovich, W. P. Weber, Tetrahedron Lett. 1975, 16, 2153. b) R.
Okazaki, K.-T. Kang, N. Inamoto, Tetrahedron Lett. 1981, 22,
235. c) D. Tzeng, R. H. Fong, H. S. D. Soysa, W. P. Weber, J.
Organomet. Chem. 1981, 219, 153. d) Y. Takeyama, K. Oshima,
K. Utimoto, Tetrahedron Lett. 1990, 31, 6059. e) K. Hirano, H.
Yorimitsu, K. Oshima, Org. Lett. 2006, 8, 483.
Reactions of silacyclobutenes with compounds other than
carbonyls: a) K.-T. Kang, H.-C. Seo, K.-N. Kim, Tetrahedron
Lett. 1985, 26, 4761. b) R. T. Conlin, S. Zhang, M. Namavari, K.
L. Bobbitt, M. J. Fink, Organometallics 1989, 8, 571. c) K.
Matsumoto, K. Oshima, K. Utimoto, Tetrahedron Lett. 1990, 31,
6055. d) K.-T. Kang, U. C. Yoon, H. C. Seo, K. N. Kim, H. Y.
Song, J. C. Lee, Bull. Korean Chem. Soc. 1991, 12, 57. e) Y.
Takeyama, K. Nozaki, K. Matsumoto, K. Oshima, K. Utimoto,
Bull. Chem. Soc. Jpn. 1991, 64, 1461. f) K. Uenishi, I. Imae, E.
Shirakawa, Y. Kawakami, Chem. Lett. 2001, 30, 986. g) K.
Uenishi, I. Imae, E. Shirakawa, Y. Kawakami, Macromolecules