10.1002/anie.201803156
Angewandte Chemie International Edition
COMMUNICATION
2013, 56, 388; f) G. K. Min, D. Hernández, T. Skrydstrup, Acc. Chem.
Res. 2013, 46, 457.
Souillart, N. Cramer, Chem. Rev. 2015, 115, 9410; g) M. Murakami, N.
Ishida, J. Am. Chem. Soc. 2016, 138, 13759; h) M. H. Shaw, J. F.
Bower, Chem. Commun. 2016, 52, 10817; i) P.-H. Chen, B. A. Billett, T.
Tsukamoto, G. Dong, ACS Catal. 2017, 7, 1340; j) G. Fumagalli, S.
Stanton, J. F. Bower, Chem. Rev. 2017, 117, 9404.
[2]
a) G. M. Cragg, D. J. Newman, Expert Opin. Invest. Drugs 2000, 9,
2783; b) E. J. Kang, E. Lee, Chem. Rev. 2005, 105, 4348; c) M. Sriram,
J. J. Hall, N. C. Grohmann, T. E. Strecker, T. Wootton, A. Franken, M. L.
Trawick, K. G. Pinney, Bioorgan. Med. Chem. 2008, 16, 8161; d) H. P.
Pepper, J. H. George, Angew. Chem. 2013, 125, 12392; Angew. Chem.
Int. Ed. 2013, 52, 12170; e) L. Nagarapu, B. Yadagiri, R. Bantu, C. G.
Kumar, S. Pombala, J. Nanubolu, Eur. J. Med. Chem. 2014, 71, 91; f) S.
Diethelm, R. Teufel, L. Kaysser, B. S. Moore, Angew. Chem. 2014, 126,
11203; Angew. Chem. Int. Ed. 2014, 53, 11023; g) Y. Sajja, S. Vanguru,
L. Jilla, H. R. Vulupala, R. Bantu, P. Yogeswari, D. Sriram, L. Nagarapu,
Bioorg. Med. Chem. Lett. 2016, 26, 4292; h) C. L. Hugelshofer, T.
Magauer, Chem. Eur. J. 2016, 22, 15125.
[8]
[9]
For recent reviews on metal-catalyzed C−Si bond cleavage, see: a) K.
Hirano, H. Yorimitsu, K. Oshima, Chem. Commun. 2008, 3234; b) Q.-W.
Zhang, K. An, W. He, Synlett 2015, 26, 1145; c) L. Li, Y. Zhang, L. Gao,
Z. Song, Tetrahedron Lett. 2015, 56, 1466; d) T. Komiyama, Y. Minami,
T. Hiyama, ACS Catal. 2017, 7, 631.
For some transition metal-catalyzed reactions of cyclopropenones, see:
a) T. Kondo, Y. Kaneko, Y. Taguchi, A. Nakamura, T. Okada, M.
Shiotsuki, Y. Ura, K. Wada, T. Mitsudo, J. Am. Chem. Soc. 2002, 124,
6824; b) P. A. Wender, T. J. Paxton, T. J. Williams, J. Am. Chem. Soc.
2006, 128, 14814; c) S. Yu, X. Li, Org. Lett. 2014, 16, 1220; d) F. Xie, S.
Yu, Z. Qi, X. Li, Angew. Chem. 2016, 128, 15577; Angew. Chem. Int.
Ed. 2016, 55, 15351; e) L. Kong, X. Zhou, Y. Xu, X. Li, Org. Lett. 2017,
19, 3644.
[3]
a) W. J. Leigh, X. Li, J. Am. Chem. Soc. 2003, 125, 8096; b) S. Díez-
González, L. Blanco, J. Organomet. Chem. 2008, 693, 2033; c) D.
Damour, A. Renaudon, S. Mignani, Synlett. 1995, 111; d) D. Damour,
M. Barreau, V. Fardin, F. Dhaleine, M. Vuilhorgne, S. Mignani, Synlett.
1998, 153.
[10] For some transition metal-catalyzed reactions of silacyclobutanes, see:
a) A. G. Myers, S. E. Kephart, H. Chen, J. Am. Chem. Soc. 1992, 114,
7922; b) S. E. Denmark, B. D. Griedel, D. M. Coe, M. E. Schnute, J.
Am. Chem. Soc. 1994, 116, 7026; c) P. R. C. Reddy, T. Hayashi, M.
Tanaka, Chem. Commun. 1996, 1865; d) Y. Tanaka, H. Yamashita, S.
Shimada, M. Tanaka, Organometallics 1997, 16, 3246; e) J. Liu, X. Sun,
M. Miyazaki, L. Liu, C. Wang, Z. Xi, J. Org. Chem. 2007, 72, 3137; f) S.
E. Denmark, J. Org. Chem. 2009, 74, 2915; g) K. Hirano, H. Yorimitsu,
K. Oshima, J. Am. Chem. Soc. 2007, 129, 6094; h) K. Hirano, H.
Yorimitsu, K. Oshima, Org. Lett. 2008, 10, 2199; i) R. Shintani, K.
Moriya, T. Hayashi, J. Am. Chem. Soc. 2011, 133, 16440; j) R. Shintani,
K. Moriya, T. Hayashi, Org. Lett. 2012, 14, 2902; k) Q.-W. Zhang, K. An,
L.-C. Liu, S. Guo, C. Jiang, H. Guo, W. He, Angew. Chem. 2016, 128,
6427; Angew. Chem. Int. Ed. 2016, 55, 6319.
[4]
[5]
For some σ-bond exchange reactions of biphenylenes, see: a) B. L.
Edelbach, R. J. Lachicotte, W. D. Jones, Organometallics 1999, 18,
4660; b) T. Matsuda, H. Kirikae, Organometallics 2011, 30, 3923.
For some examples on σ-bond cross exchange reactions of
alkylidenecyclopropanes, see: a) N. Chatani, T. Takeyasu, T. Hanafusa,
Tetrahedron Lett. 1988, 29, 3979; b) T. Pohlmann, A. de Meijere, Org.
Lett. 2000, 2, 3877; c) M. Suginome, T. Matsuda, Y. Ito, J. Am. Chem.
Soc. 2000, 122, 11015; d) Z.-L. Cheng, J.-C. Xiao, C. Liu, Q.-Y. Chen,
Eur. J. Org. Chem. 2006, 5581; e) S. Saito, T. Yoshizawa, S. Ishigami,
R. Yamasaki, Tetrahedron Lett. 2010, 51, 6028.
[6]
[7]
For the σ-bond cross exchange reactions of (benzo)cyclobutanones,
see: a) N. Ishida, W. Ikemoto, M. Murakami, Org. Lett. 2012, 14, 3230;
b) N. Ishida, W. Ikemoto, M. Murakami, J. Am. Chem. Soc. 2014, 136,
5912; c) S. Okumura, F. Sun, N. Ishida, M. Murakami, J. Am. Chem.
Soc. 2017, 139, 12414.
[11] CCDC 1828415 (3a) and CCDC 1828412 (5a) contain the
supplementary crystallographic data. These data can be obtained free
of charge from The Cambridge Crystallographic Data Centre via
For some recent reviews on metal-catalyzed C−C bond cleavage, see:
a) C.-H. Jun, Chem. Soc. Rev. 2004, 33, 610; b) M. Tobisu, N. Chatani,
Chem. Soc. Rev. 2008, 37, 300; c) S. M. Bonesi, M. Fagnoni, Chem.
Eur. J. 2010, 16, 13572; d) D. J. Mack, J. T. Njardarson, ACS Catal.
2013, 3, 272; d) F. Chen, T. Wang, N. Jiao, Chem. Rev. 2014, 114,
8613; e) H. Liu, M. Feng, X. Jiang, Chem. Asian J. 2014, 9, 3360; f) L.
[12] a) R. Okazaki, K. T. Kang, N. Inamoto, Tetrahedron Lett. 1981, 22, 235;
b) Y. Takeyama, K. Oshima, K. Utimoto, Tetrahedron Lett. 1990, 31,
6059.
[13] M. M. Aborways, W. J. Moran, J. Organomet. Chem. 2015, 797, 57.
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