Paper
Organic & Biomolecular Chemistry
2
014, 16, 3990–3993; (k) S. Tang, Y.-L. Deng, J. Li,
and A. Togni, Tetrahedron: Asymmetry, 2006, 17, 658–664;
(d) Y. Hamashima, T. Suzuki, H. Takano, Y. Shimura,
Y. Tsuchiya, K.-i. Moriya, T. Goto and M. Sodeoka,
Tetrahedron, 2006, 62, 7168–7179; (e) T. Suzuki, T. Goto,
Y. Hamashima and M. Sodeoka, J. Org. Chem., 2007, 72,
246–250; (f) D. S. Reddy, N. Shibata, J. Nagai, S. Nakamura,
T. Toru and S. Kanemasa, Angew. Chem., Int. Ed., 2008, 47,
164–168; (g) T. J. Nash and G. Pattison, Eur. J. Org. Chem.,
2015, 3779–3786; (h) K. Hayamizu, N. Terayama,
D. Hashizume, K. Dodo and M. Sodeoka, Tetrahedron,
2015, 71, 6594–6601; (i) Y. e. You, L. Zhang and S. Luo,
Chem. Sci., 2017, 8, 621–626.
W.-X. Wang, G.-L. Ding, M.-W. Wang, Z.-P. Xiao, Y.-C. Wang
and R.-L. Sheng, J. Org. Chem., 2015, 80, 12599–12605;
(
l) X. Yang, T. Wu, R. J. Phipps and F. D. Toste, Chem. Rev.,
015, 115, 826–870; (m) P. A. Champagne, J. Desroches,
J.-D. Hamel, M. Vandamme and J.-F. Paquin, Chem. Rev.,
015, 115, 9073–9174; (n) M. G. Campbell and T. Ritter,
2
2
Chem. Rev., 2015, 115, 612–633; (o) D. E. Yerien, S. Bonesi
and A. Postigo, Org. Biomol. Chem., 2016, 14, 8398–8427;
(
2
p) X.-S. Xue, Y. Wang, M. Li and J.-P. Cheng, J. Org. Chem.,
016, 81, 4280–4289; (q) S. Tang, L. Yuan, Y.-L. Deng,
Z.-Z. Li, L.-N. Wang, G.-X. Huang and R.-L. Sheng,
Tetrahedron Lett., 2017, 58, 329–332.
Selected examples on C(sp )–F bond formation reaction,
7 L. Hintermann and A. Togni, Angew. Chem., Int. Ed., 2000,
39, 4359–4362.
2
4
see: (a) P. S. Fier, J. Luo and J. F. Hartwig, J. Am. Chem. Soc.,
8 (a) M. Althaus, C. Becker, A. Togni and A. Mezzetti,
Organometallics, 2007, 26, 5902–5911; (b) M. Althaus,
A. Togni and A. Mezzetti, J. Fluorine Chem., 2009, 130, 702–
707; (c) L. Wang, W. Meng, C.-L. Zhu, Y. Zheng, J. Nie and
J.-A. Ma, Angew. Chem., Int. Ed., 2011, 50, 9442–9446;
(d) A. Narayama, K. Shibatomi, Y. Soga, T. Muto and
S. Iwasa, Synlett, 2013, 24, 375–378; (e) H. Lee, J. Börgel and
T. Ritter, Angew. Chem., Int. Ed., 2017, 56, 6966–6969;
(f) Y. Wang, H. Wang, Y. Jiang, C. Zhang, J. Shao and
D. Xu, Green Chem., 2017, 19, 1674–1677.
9 Selected reviews on metal–carbene, see: (a) M. P. Doyle,
Chem. Rev., 1986, 86, 919–939; (b) M. P. Doyle and
D. C. Forbes, Chem. Rev., 1998, 98, 911–936; (c) Y. Xia,
Y. Zhang and J. Wang, ACS Catal., 2013, 3, 2586–2598;
(d) M. Jia and S. Ma, Angew. Chem., Int. Ed., 2016, 55, 9134–
9166; (e) B. Wang, D. Qiu, Y. Zhang and J. Wang, Beilstein
J. Org. Chem., 2016, 12, 796–804; (f) Y. Xia, D. Qiu and
J. Wang, Chem. Rev., 2017, 117, 13810–13889.
2
013, 135, 2552–2559; (b) Y. Ye and M. S. Sanford, J. Am.
Chem. Soc., 2013, 135, 4648–4651; (c) A. F. Brooks,
J. J. Topczewski, N. Ichiishi, M. S. Sanford and
P. J. H. Scott, Chem. Sci., 2014, 5, 4545–4553;
(
d) C. N. Neumann, J. M. Hooker and T. Ritter, Nature,
016, 534, 369; (e) K. J. Makaravage, A. F. Brooks,
A. V. Mossine, M. S. Sanford and P. J. H. Scott, Org. Lett.,
016, 18, 5440–5443; (f) H. Shi, A. Braun, L. Wang,
S. H. Liang, N. Vasdev and T. Ritter, Angew. Chem., Int. Ed.,
016, 55, 10786–10790; (g) S. D. Schimler, M. A. Cismesia,
2
2
2
P. S. Hanley, R. D. J. Froese, M. J. Jansma, D. C. Bland and
M. S. Sanford, J. Am. Chem. Soc., 2017, 139, 1452–1455;
(
1
h) X.-Y. Chen and E. J. Sorensen, J. Am. Chem. Soc., 2018,
40, 2789–2792.
3
5
Selected examples on C(sp )–F bond formation reaction,
see: (a) X.-Y. Chen and E. J. Sorensen, J. Am. Chem. Soc.,
2
018, 140, 2789–2792; (b) K. L. Hull, W. Q. Anani and
M. S. Sanford, J. Am. Chem. Soc., 2006, 128, 7134–7135; 10 Selected examples on metal–carbene coupling, see:
c) K.-i. Moriya, Y. Hamashima and M. Sodeoka, Synlett,
007, 1139–1142; (d) V. Rauniyar, A. D. Lackner,
G. L. Hamilton and F. D. Toste, Science, 2011, 334, 1681–
684; (e) S. Suzuki, Y. Kitamura, S. Lectard, Y. Hamashima
and M. Sodeoka, Angew. Chem., Int. Ed., 2012, 51, 4581–
585; (f) X. Yang, R. J. Phipps and F. D. Toste, J. Am. Chem.
(
2
(a) W.-W. Chan, S.-F. Lo, Z. Zhou and W.-Y. Yu, J. Am.
Chem. Soc., 2012, 134, 13565–13568; (b) X. Yu, S. Yu,
J. Xiao, B. Wan and X. Li, J. Org. Chem., 2013, 78, 5444–
5452; (c) F. Hu, Y. Xia, F. Ye, Z. Liu, C. Ma, Y. Zhang and
J. Wang, Angew. Chem., Int. Ed., 2014, 53, 1364–1367;
(d) J. Jeong, P. Patel, H. Hwang and S. Chang, Org. Lett.,
2014, 16, 4598–4601; (e) B. Ye and N. Cramer, Angew.
Chem., Int. Ed., 2014, 53, 7896–7899; (f) H.-W. Lam,
K.-Y. Man, W.-W. Chan, Z. Zhou and W.-Y. Yu, Org. Biomol.
Chem., 2014, 12, 4112–4116; (g) F.-N. Ng, Y.-F. Lau, Z. Zhou
and W.-Y. Yu, Org. Lett., 2015, 17, 1676–1679;
(h) S. Sharma, S. H. Han, S. Han, W. Ji, J. Oh, S.-Y. Lee,
J. S. Oh, Y. H. Jung and I. S. Kim, Org. Lett., 2015, 17, 2852–
2855; (i) Y.-S. Lu and W.-Y. Yu, Org. Lett., 2016, 18, 1350–
1353; ( j) J. Wu, D. Wang, Y. Wan and C. Ma, Chem.
Commun., 2016, 52, 1661–1664; (k) S. Allu, M. Ravi and
K. C. Kumara Swamy, Eur. J. Org. Chem., 2016, 5697–5705;
(l) Z. Hu and G. Liu, Adv. Synth. Catal., 2017, 359, 1643–
1648.
1
4
Soc., 2014, 136, 5225–5228; (g) J.-A. Ma and S. Li, Org.
Chem. Front., 2014, 1, 712–715; (h) K. Mori, A. Miyake and
T. Akiyama, Chem. Lett., 2014, 43, 137–139; (i) J. Miao,
K. Yang, M. Kurek and H. Ge, Org. Lett., 2015, 17, 3738–
3
741; ( j) N. W. Goldberg, X. Shen, J. Li and T. Ritter, Org.
Lett., 2016, 18, 6102–6104; (k) M. S. McCammant,
S. Thompson, A. F. Brooks, S. W. Krska, P. J. H. Scott and
M. S. Sanford, Org. Lett., 2017, 19, 3939–3942; (l) W. Liu,
X. Huang, M. S. Placzek, S. W. Krska, P. McQuade,
J. M. Hooker and J. T. Groves, Chem. Sci., 2018, 9, 1168–
1
172.
Selected examples on electrophilic C(sp )–F bond for-
mation on 1,3-dicarbonyl compounds, see:
a) Y. Hamashima, K. Yagi, H. Takano, L. Tamás and 11 X. Ma, J. Jiang, S. Lv, W. Yao, Y. Yang, S. Liu, F. Xia and
M. Sodeoka, J. Am. Chem. Soc., 2002, 124, 14530–14531; W. Hu, Angew. Chem., Int. Ed., 2014, 53, 13136–13139.
b) Y. Hamashima, H. Takano, D. Hotta and M. Sodeoka, 12 (a) H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park and
3
6
(
(
Org. Lett., 2003, 5, 3225–3228; (c) D. P. Huber, K. Stanek
K. Itoh, J. Am. Chem. Soc., 1994, 116, 2223–2224;
Org. Biomol. Chem.
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