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Notes and references
1 For selected examples, see: (a) W. Liu, M. Buck, N. Chen, M. Shang,
N. J. Taylor, J. Asoud, X. Wu, B. B. Hasinoff and G. I. Dmitrienko, Org.
Lett., 2007, 9, 2915–2918; (b) J. H. Ahn, M. S. Shin, S. H. Jung,
S. K. Kang, K. R. Kim, S. D. Rhee, W. H. Jung, S. D. Yang, S. J. Kim,
J. R. Woo, J. H. Lee, H. G. Cheon and S. S. Kim, J. Med. Chem., 2006,
49, 4781–4784; (c) R. E. McDevitt, M. S. Malamas, E. S. Manas,
R. J. Unwalla, Z. B. Xu, C. P. Miller and H. A. Harris, Bioorg. Med.
Chem. Lett., 2005, 15, 3137–3142; (d) C. H. Park, X. Siomboing,
S. Yous, B. Gressier, M. Luyckx and P. Chavatte, Eur. J. Med. Chem.,
2001, 37, 461–468; (e) M. A. Ernst-Russell, C. L. L. Chai, J. H. Wardlaw
and J. A. Elix, J. Nat. Prod., 2000, 63, 129–131; ( f ) W. M. Clark,
A. M. Tickner-Eldridge, G. K. Huang, L. N. Pridgen, M. A. Olsen,
R. J. Mills, I. Lantos and N. H. Baine, J. Am. Chem. Soc., 1998, 120,
4550–4551; (g) L. M. X. Lopes, M. Yoshida and O. R. Gottlieb,
Phytochemistry, 1984, 23, 2021–2024; (h) K.-M. E. Ng and
T. C. Mcmorris, Can. J. Chem., 1984, 62, 1945–1953; (i) N. Tanaka,
T. Satake, A. Takahashi, M. Mochizuki, T. Murakami, Y. Saiki, J.-Z.
Yang and C.-M. Chen, Chem. Pharm. Bull., 1982, 30, 3640–3646;
( j) S. Sengupta, M. Sen, S. K. Niyogi, S. C. Pakrashi and E. Ali,
Phytochemistry, 1976, 15, 995–998.
2 For selected examples, see: (a) C. Pan, B. Huang, W. Hu, X. Feng and
J.-T. Yu, J. Org. Chem., 2016, 81, 2087–2093; (b) Y. Yokoyama, Y. Unoh,
R. A. Bohmann, T. Satoh, K. Hirano, C. Bolm and M. Miura, Chem. Lett.,
2015, 44, 1104–1106; (c) D. H. Dethe and G. M. Murhade, Chem.
Commun., 2015, 51, 10891–10894; (d) K. R. Babu and F. A. Khan, Org.
Biomol. Chem., 2015, 13, 299–308; (e) X. Yan, S. Zou, P. Zhao and C. Xi,
Chem. Commun., 2014, 50, 2775–2777; ( f ) B.-J. Li, H.-Y. Wang, Q.-L. Zhu
and Z.-J. Shi, Angew. Chem., Int. Ed., 2012, 51, 3948–3952; (g) X. Chen,
J. Jin, N. Wang, P. Lu and Y. Wang, Eur. J. Org. Chem., 2012, 824–830;
(h) Y. Kuninobu, T. Matsuki and K. Takai, Org. Lett., 2010, 12,
2948–2950; (i) T. Morimoto, K. Yamasaki, A. Hirano, K. Tsutsumi,
N. Kagawa, K. Kakiuchi, Y. Harada, Y. Fukumoto, N. Chatani and
T. Nishioka, Org. Lett., 2009, 11, 1777–1780; ( j) Y. Harada, J. Nakanishi,
H. Fujihara, M. Tobisu, Y. Fukumoto and N. Chatani, J. Am. Chem. Soc.,
2007, 129, 5766–5771; (k) S. Walspurger, A. V. Vasilyev, J. Sommer and
P. Pale, Tetrahedron, 2005, 61, 3559–3564; (l) R. C. Larock, Q. Tian and
A. A. Pletnev, J. Am. Chem. Soc., 1999, 121, 3238–3239; (m) D. C.
Harrowven, N. A. Newman and C. A. Knight, Tetrahedron Lett., 1998,
39, 6757–6760; (n) T. Fukuyama, N. Chatani, F. Kakiuchi and S. Murai,
J. Org. Chem., 1997, 62, 5647–5650; (o) K. Kokubo, K. Matsumasa,
M. Miura and M. Nomura, J. Org. Chem., 1996, 61, 6941–6946;
(p) R. C. Larock and M. J. Doty, J. Org. Chem., 1993, 58, 4579–4583;
(q) R. L. Frank, H. Eklund, J. W. Richter, C. R. Vanneman and
A. N. Wennerberg, J. Am. Chem. Soc., 1944, 66, 1–4.
Scheme 1 Regioselective synthesis of 2,3-diaryl indenones 5a and 5d.
3 (a) J. L. Jeffrey and R. Sarpong, Org. Lett., 2009, 11, 5450–5453;
(b) S. A. Snyder, S. P. Breazzano, A. G. Ross, Y. Lin and A. L. Zografos,
J. Am. Chem. Soc., 2009, 131, 1753–1765; (c) S. A. Snyder, A. L. Zografos
and Y. Lin, Angew. Chem., Int. Ed., 2007, 46, 8186–8191; (d) W. Li, H. Li,
Y. Li and Z. Hou, Angew. Chem., Int. Ed., 2006, 45, 7609–7611; (e) T. Ito,
T. Tanaka, M. Iinuma, K. Nakaya, Y. Takahashi, R. Sawa, J. Murata and
D. Darnaedi, J. Nat. Prod., 2004, 67, 932–937; ( f ) S. A. Adesanya, R. Nia,
Scheme 2 Proposed reaction mechanism.
decrease in regioselectivity (3i and 3j in Table 1). In the case
where 1-trimethylsilyl-3,3-dimethyl-1-butyne and bis(trimethylsilyl)-
acetylene were used as bulky silyl alkynes, the reaction did not
proceed. These results reveal that the [Co]–carbon bond of
complex II does not likely prefer a sterically bulky group.
In conclusion, we have demonstrated that the Co-catalyzed
system is useful for achieving [3+2] annulation of o-methoxy-
carbonylphenylboronic acid and alkynes leading to the formation
of 2,3-disubstituted indenones. Interestingly, when silyl alkynes
were used, regioselective annulation took place to give 3-silyl-
substituted indenones. The resulting vinylsilane moiety of 3-silyl
indenones was readily converted to a vinylarene moiety by a
bromination/cross-coupling protocol, enabling regio-controlled
synthesis of 2,3-diaryl substituted indenones.
¨
M.-T. Martin, N. Boukamcha, A. Montagnac and M. Paıs, J. Nat. Prod.,
1999, 62, 1694–1695; (g) T. Tanaka, M. Iinuma and H. Murata,
Phytochemistry, 1998, 48, 1045–1049; (h) G. M. Anstead, J. L. Ensign,
C. S. Peterson and J. A. Katzenellenbogen, J. Org. Chem., 1989, 54,
1485–1491; (i) G. M. Anstead, S. R. Wilson and J. A. Katzenellenbogen,
J. Med. Chem., 1989, 32, 2163–2171; ( j) G. M. Anstead, R. J. Altenbach,
S. R. Wilson and J. A. Katzenellenbogen, J. Med. Chem., 1988, 31,
1316–1326; (k) E. F. Ullman and W. A. Henderson, Jr., J. Am. Chem.
Soc., 1966, 88, 4942–4960.
4 (a) B. Gourdet, M. E. Rudkin and H. W. Lam, Org. Lett., 2010, 12,
2554–2557; (b) F. Zhou, M. Yang and X. Lu, Org. Lett., 2009, 11,
1405–1408; (c) M. Miyamoto, Y. Harada, M. Tobisu and N. Chatani,
Org. Lett., 2008, 10, 2975–2978; (d) M. Yang, X. Zhang and X. Lu, Org.
Lett., 2007, 9, 5131–5133; (e) G. Liu and X. Lu, Adv. Synth. Catal., 2007,
349, 2247–2252; ( f ) T. Matsuda, M. Makino and M. Murakami,
Chem. Lett., 2005, 34, 1416–1417; (g) R. Shintani, K. Okamoto and
T. Hayashi, Chem. Lett., 2005, 34, 1294–1295; (h) M. Lautens and
T. Marquardt, J. Org. Chem., 2004, 69, 4607–4614.
This work was supported by a Grant-in-Aid for Scientific
Research from the MEXT and the JSPS (26105752 for MU;
26248031 for IR).
5 T. Miura and M. Murakami, Org. Lett., 2005, 7, 3339–3341. Also see
the following corrections: T. Miura and M. Murakami, Org. Lett.,
2006, 8, 1961.
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