Organic Letters
Letter
Muijlwijk-Koezen, J. E.; Timmerman, H.; Link, R.; van der Goot, H.;
Ijzerman, A. P. J. Med. Chem. 1998, 41, 3987. (h) Cho, W.-J.; Kim, E.-
K.; Park, I. Y.; Jeong, E. Y.; Kim, T. S.; Le, T. N.; Kim, D.-D.; Lee, E.-S.
Bioorg. Med. Chem. 2002, 10, 2953. (i) Yang, S. H.; Van, H. T. M.; Le,
T. N.; Khadka, D. B.; Cho, S. H.; Lee, K.-T.; Lee, E.-S.; Lee, Y. B.;
Ahn, C.-H.; Cho, W.-J. Eur. J. Med. Chem. 2010, 45, 5493. (j) Marco,
E.; Laine, W.; Tardy, C.; Lansiaux, A.; Iwao, M.; Ishibashi, F.; Bailly,
C.; Gago, F. J. Med. Chem. 2005, 48, 3796. (k) Tsuboyama, A.;
Iwawaki, H.; Furugori, M.; Mukaide, T.; Kamatani, J.; Igawa, S.;
Moriyama, T.; Miura, S.; Takiguchi, T.; Okada, S.; Hoshino, M.; Ueno,
K. J. Am. Chem. Soc. 2003, 125, 12971.
(2) For selected reviews, see: (a) Chrzanowska, M.; Grajewska, A.;
Rozwadowska, M. D. Chem. Rev. 2016, 116, 12369. (b) Zhang, B.;
Studer, A. Chem. Soc. Rev. 2015, 44, 3505. (c) Jin, R.; Patureau, F. W.
ChemCatChem 2015, 7, 223. (d) Alvarez, M.; Joule, J. A. Sci. Synth.
2005, 15, 661. (e) Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev.
2004, 104, 3341.
(3) (a) Bischler, A.; Napieralski, B. Ber. Dtsch. Chem. Ges. 1893, 26,
1903. (b) Xu, X.; Guo, S.; Dang, Q.; Chen, J.; Bai, X. J. Comb. Chem.
2007, 9, 773. (c) Heravi, M. M.; Khaghaninejad, S.; Nazari, N. Adv.
Heterocycl. Chem. 2014, 112, 183. (d) Heravi, M. M.; Nazari, N. Curr.
Org. Chem. 2015, 19, 2358. (e) Pomeranz, C. Monatsh. Chem. 1893,
14, 116. (f) Fritsch, P. Ber. Dtsch. Chem. Ges. 1893, 26, 419. (g) Herz,
W.; Tocker, S. J. Am. Chem. Soc. 1955, 77, 6355. (h) Pictet, A.;
Spengler, T. Ber. Dtsch. Chem. Ges. 1911, 44, 2030. (i) Cox, E. D.;
Cook, J. M. Chem. Rev. 1995, 95, 1797.
(4) For selected reviews, see: (a) Nakamura, I.; Yamamoto, Y. Chem.
Rev. 2004, 104, 2127. (b) Zeni, G.; Larock, R. C. Chem. Rev. 2004,
104, 2285. (c) He, R.; Huang, Z.-T.; Zheng, Q.-Y.; Wang, C.
Tetrahedron Lett. 2014, 55, 5705. (d) Herraiz-Cobo, J.; Albericio, F.;
Alvarez, M. Adv. Heterocycl. Chem. 2015, 116, 1. (e) Huang, H.; Cai, J.;
Deng, G.-J. Org. Biomol. Chem. 2016, 14, 1519.
(x) Helan, V.; Gulevich, A. V.; Gevorgyan, V. Chem. Sci. 2015, 6, 1928.
(y) Shi, Y.; Gevorgyan, V. Chem. Commun. 2015, 51, 17166. (z) Joshi,
A.; Chandra Mohan, D.; Adimurthy, S. Org. Lett. 2016, 18, 464. [Ag]:
(aa) Liu, R.; Zhang, M.; Winston-McPherson, G.; Tang, W. Chem.
Commun. 2013, 49, 4376.
(7) (a) Jiang, Y.; Sun, R.; Wang, Q.; Tang, X.-Y.; Shi, M. Chem.
Commun. 2015, 51, 16968. (b) Sun, R.; Jiang, Y.; Tang, X.-Y.; Shi, M.
Chem. - Eur. J. 2016, 22, 5727. (c) Yu, Y.; Zhu, L.; Liao, Y.; Mao, Z.;
Huang, X. Adv. Synth. Catal. 2016, 358, 1059. (d) He, J.; Shi, Y.-P.;
Cheng, W.-L.; Man, Z.-M.; Yang, D.-D.; Li, C.-Y. Angew. Chem., Int.
Ed. 2016, 55, 4557. (e) Shen, H.; Fu, J.; Gong, J.; Yang, Z. Org. Lett.
2014, 16, 5588. (f) Sun, R.; Jiang, Y.; Tang, X.-Y.; Shi, M. Asian J. Org.
Chem. 2017, 6, 83.
(8) For leading papers and reviews on the silver(I) carbenoid, see:
(a) Dias, H. V. R.; Browning, R. G.; Polach, S. A.; Diyabalanage, H. V.
K.; Lovely, C. J. J. Am. Chem. Soc. 2003, 125, 9270. (b) Caballero, A.;
Despagnet-Ayoub, E.; Díaz-Requejo, M. M.; Díaz-Rodríguez, A.;
Gonzal
G.; Etienne, M.; Per
Komine, N.; Pal, K.; Pinter, B.; Pink, M.; Chen, C.-H.; Caulton, K. G.;
́
ez-Nunez, M. E.; Mello, R.; Munoz, B. K.; Ojo, W.-S.; Asensio,
́
̃
̃
́
ez, P. J. Science 2011, 332, 835. (c) Flores, J. A.;
Mindiola, D. J. ACS Catal. 2012, 2, 2066. (d) Doyle, M. P.
ChemCatChem 2011, 3, 1681. (e) Caballero, A.; Perez, P. J. J.
́
Organomet. Chem. 2015, 793, 108. (f) Hussong, M. W.; Hoffmeister,
W. T.; Rominger, F.; Straub, B. F. Angew. Chem., Int. Ed. 2015, 54,
10331. (g) Luo, H.; Wu, G.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed.
2015, 54, 14503. (h) Liu, Z.; Li, Q.; Liao, P.; Bi, X. Chem. - Eur. J.
2017, 23, 4756. (i) Naodovic, M.; Yamamoto, H. Chem. Rev. 2008,
108, 3132. (j) Weibel, J.-M.; Blanc, A.; Pale, P. Chem. Rev. 2008, 108,
3149. (k) Silver in Organic Chemistry; Harmata, M., Ed.; John Wiley &
Sons, Inc.: Hoboken, NJ, 2010. (l) Fang, G.; Bi, X. Chem. Soc. Rev.
2015, 44, 8124. (m) Zheng, Q.-Z.; Jiao, N. Chem. Soc. Rev. 2016, 45,
4590.
(9) CCDC 1447728 (3ka) and CCDC 1447726 (4v).
(5) (a) Chattopadhyay, B.; Gevorgyan, V. Angew. Chem., Int. Ed.
2012, 51, 862. (b) Gulevich, A. V.; Gevorgyan, V. Angew. Chem., Int.
Ed. 2013, 52, 1371. (c) Davies, H. M. L.; Alford, J. S. Chem. Soc. Rev.
2014, 43, 5151. (d) Moderhack, D. Heterocycles 2014, 89, 2053.
(e) Huang, J.; Zhou, H.; Chen, Z. Youji Huaxue 2016, 36, 1555.
(f) Jiang, Y.; Sun, R.; Tang, X.-Y.; Shi, M. Chem. - Eur. J. 2016, 22,
17910. (g) Jia, M.; Ma, S. Angew. Chem., Int. Ed. 2016, 55, 9134.
(6) For representative papers on the transannulation reactions using
[Rh], see: (a) Chuprakov, S.; Hwang, F. W.; Gevorgyan, V. Angew.
Chem., Int. Ed. 2007, 46, 4757. (b) Horneff, T.; Chuprakov, S.;
Chernyak, N.; Gevorgyan, V.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130,
14972. (c) Chuprakov, S.; Kwok, S.; Zhang, W. L.; Lercher, L.; Fokin,
V. V. J. Am. Chem. Soc. 2009, 131, 18034. (d) Chuprakov, S.; Kwok, S.
W.; Fokin, V. V. J. Am. Chem. Soc. 2013, 135, 4652. (e) Zibinsky, M.;
Fokin, V. V. Angew. Chem., Int. Ed. 2013, 52, 1507. (f) Parr, B. T.;
Davies, H. M. L. Angew. Chem., Int. Ed. 2013, 52, 10044. (g) Shi, Y.;
Gevorgyan, V. Org. Lett. 2013, 15, 5394. (h) Parr, T.; Green, S. A.;
Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 4716. (i) Spangler, J. E.;
Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 6802. (j) Miura, T.;
Funakoshi, Y.; Murakami, M. J. Am. Chem. Soc. 2014, 136, 2272.
(k) Yang, J.-M.; Zhu, C.-Z.; Tang, X.-Y.; Shi, M. Angew. Chem., Int. Ed.
2014, 53, 5142. (l) Chen, K.; Zhu, Z.-Z.; Zhang, Y.-S.; Tang, X.-Y.; Shi,
M. Angew. Chem., Int. Ed. 2014, 53, 6645. (m) Tang, X.-Y.; Zhang, Y.-
S.; He, L.; Wei, Y.; Shi, M. Chem. Commun. 2015, 51, 133. (n) Shang,
H.; Wang, Y.; Tian, Y.; Feng, J.; Tang, Y. Angew. Chem., Int. Ed. 2014,
53, 5662. (o) Yang, Y.; Zhou, M.-B.; Ouyang, X.-H.; Pi, R.; Song, R.-J.;
Li, J.-H. Angew. Chem., Int. Ed. 2015, 54, 6595. (p) Man, Z.; Dai, H.;
Shi, Y.; Yang, D.; Li, C.-Y. Org. Lett. 2016, 18, 4962. (q) Liu, S.; Yao,
W.; Liu, Y.; Wei, Q.; Chen, J.; Wu, X.; Xia, F.; Hu, W. Sci. Adv. 2017,
3, e1602467. [Ni]: (r) Miura, T.; Yamauchi, M.; Murakami, M. Chem.
Commun. 2009, 1470. (s) Miura, T.; Hiraga, K.; Biyajima, T.;
Nakamuro, T.; Murakami, M. Org. Lett. 2013, 15, 3298. [Pd]:
(t) Nakamura, I.; Nemoto, T.; Shiraiwa, N.; Terada, M. Org. Lett.
2009, 11, 1055. (u) Miura, T.; Nishida, Y.; Morimoto, M.; Yamauchi,
M.; Murakami, M. Org. Lett. 2011, 13, 1429. (v) Moon, Y.; Kwon, S.;
Kang, D.; Im, H.; Hong, S. Adv. Synth. Catal. 2016, 358, 958.
(w) Wang, Y.; Wu, Y.; Li, Y.; Tang, Y. Chem. Sci. 2017, 8, 3852. [Cu]:
D
Org. Lett. XXXX, XXX, XXX−XXX