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were afforded from their corresponding biphenyl derivatives,
which can be readily prepared. This new method is also
applicable to the synthesis of spirosilabifluorenes and silicon-
bridged terphenyl derivatives. In addition, we have demon-
strated the transformation of the amino groups in the sila-
fluorene derivatives into several other substituents. We hope
that the developed reaction will become a useful and effective
protocol to synthesize a variety of silafluorene derivatives.
This work was supported in part by JSPS KAKENHI Grant
Numbers JP 17H03016 and 18H04656, Iketani Science and
Technology Foundation, The Sumitomo Foundation, and A-STEP
8 For examples of the synthesis of silafluorene derivatives by intra-
molecular cyclization via silyl radicals, see: (a) D. Leifert and
A. Studer, Org. Lett., 2015, 17, 386; (b) L. Xu, S. Zhang and P. Li,
Org. Chem. Front., 2015, 2, 459.
9 (a) T. Ureshino, T. Yoshida, Y. Kuninobu and K. Takai, J. Am. Chem.
Soc., 2010, 132, 14324; (b) Y. Kuninobu, K. Yamauchi, N. Tamura,
T. Seiki and K. Takai, Angew. Chem., Int. Ed., 2013, 52, 1520.
0 M. Murata, M. Takizawa, H. Sasaki, Y. Kohari, H. Sakagami,
T. Namikoshi and S. Watanabe, Chem. Lett., 2016, 45, 857.
1 S. C. Richter and M. Oestreich, Trends Chem., DOI: 10.1016/
j.trechm.2019.07.003.
1
1
1
2 (a) T. Matsuda, S. Kadowaki, T. Goya and M. Murakami, Org. Lett., 2007,
9, 133; (b) M. Shimizu, K. Mochida and T. Hiyama, Angew. Chem., Int. Ed.,
2
008, 47, 9760; (c) Y. Yabusaki, N. Ohshima, H. Kondo, T. Kusamoto,
Y. Yamanoi and H. Nishihara, Chem. – Eur. J., 2010, 16, 5581;
d) J. M. Breunig, P. Gupta, A. Das, S. Tussupbayev, M. Diefenbach,
(VP30218088652) from JST.
(
M. Bolte, M. Wagner, M. C. Holthausen and H.-W. Lerner, Chem. – Asian
J., 2014, 9, 3163.
3 Y. Ma, B. Wang, L. Zhang and Z. Hou, J. Am. Chem. Soc., 2016,
1
1
Conflicts of interest
1
38, 3663.
4 For other C–H silylation via sila-Friedel–Crafts reaction, see;
a) S. B ¨a hr and M. Oestreich, Angew. Chem., Int. Ed., 2017, 56, 52.
There are no conflicts to declare.
(
For an example of Brønsted or Lewis acid-catalyzed sila-Friedel–
Crafts reaction, see: (b) Q.-A. Chen, H. F. T. Klare and M. Oestreich,
J. Am. Chem. Soc., 2016, 138, 7868; (c) Q. Yin, H. F. T. Klare and
M. Oestreich, Angew. Chem., Int. Ed., 2016, 55, 3204.
Notes and references
1
(a) R.-F. Chen, Q.-L. Fan, S.-J. Liu, R. Zhu, K.-Y. Pu and W. Huang,
Synth. Met., 2006, 156, 1161; (b) K. Mouri, A. Wakamiya, H. Yamada, 15 L. Omann and M. Oestreich, Organometallics, 2017, 36, 767.
T. Kajiwara and S. Yamaguchi, Org. Lett., 2007, 9, 93; (c) J. C. Sanchez, 16 The structure of 3b was determined by single crystal X-ray structure
A. G. DiPasquale, A. L. Rheingold and W. C. Trogler, Chem. Mater.,
analysis. For the details, see the ESI.† CCDC 1950091 (3b).
2
007, 19, 6459; (d) E. Wang, C. Li, W. Zhuang, J. Peng and Y. Cao, 17 For selected papers for the synthesis and optoelectronic properties
J. Mater. Chem., 2008, 18, 797; (e) J. C. Sanchez and W. C. Trogler,
J. Mater. Chem., 2008, 18, 3143; ( f ) Y.-Q. Mo, X.-Y. Deng, X. Jiang and
Q.-H. Cui, J. Polym. Sci., Part A: Polym. Chem., 2009, 47, 3286.
(a) S. Beaupre, P.-L. T. Boudreault and M. Leclerc, Adv. Mater., 2010,
of spirosilabifluorenes, see: (a) A. G. Russell, N. S. Spencer, D. Philp,
B. M. Kariuki and J. S. Snaith, Organometallics, 2003, 22, 5589;
(b) S. H. Lee, B.-B. Jang and Z. H. Kafafi, J. Am. Chem. Soc., 2005,
127, 9071; (c) H. Xiao, B. Leng and H. Tian, Polymer, 2005, 46, 5707;
(d) T. Agou, M. D. Hossain and T. Kawashima, Chem. – Eur. J., 2010,
16, 368; (e) S. Furakawa, J. Kobayashi and T. Kawashima, Dalton
Trans., 2010, 39, 9329; ( f ) E. Pusztai, I. S. Toulokhonova, N. Temple,
H. Albright, U. I. Zakai, S. Guo, I. A. Guzei, R. Hu and R. West,
Organometallics, 2013, 32, 2529; (g) A. V. Zabula, A. Y. Rogachev,
I. A. Guzei and R. West, Organometallics, 2013, 32, 3760; (h) M. Murai,
Y. Takeuchi, K. Yamauchi, Y. Kuninobu and K. Takai, Chem. – Eur. J.,
2016, 22, 6048.
2
3
2
2, E6; (b) J. Y. Corey, Adv. Organomet. Chem., 2011, 59, 1.
(a) H. Usta, G. Lu, A. Facchetti and T. J. Marks, J. Am. Chem. Soc.,
006, 128, 9034; (b) G. Lu, H. Usta, C. Risko, L. Wang, A. Facchetti,
2
M. A. Ratner and T. J. Marks, J. Am. Chem. Soc., 2008, 130, 7670.
(a) J. Hou, H.-Y. Chen, S. Zhang, G. Li and Y. Yang, J. Am. Chem. Soc.,
4
2
008, 130, 16144; (b) Y. Zou, D. Gendron, R. Neagu-Plesu and
M. Leclerc, Macromolecules, 2009, 42, 6361.
5
6
H. Gilman and R. D. Gorsich, J. Am. Chem. Soc., 1955, 77, 6380.
For ruthenium-catalyzed reactions, see: (a) L. Omann and M. Oestreich, 18 L. Li, J. Xiang and C. Xu, Org. Lett., 2007, 9, 4877.
Angew. Chem., Int. Ed., 2015, 54, 10276; (b) S. B ¨a hr, A. Simonneau, 19 (a) H. N. Shin, C. S. Kim, Y. J. Cho, H. J. Kwon, B. O. Kim, S. M. Kim
E. Irran and M. Oestreich, Organometallics, 2016, 35, 925.
An example of a stoichiometric reaction: (a) S. Furukawa, J. Kobayashi
and T. Kawashima, J. Am. Chem. Soc., 2009, 131, 14192. An example of
and S. S. Yoon, WO 2010114243, Dow Advanced Display Materials,
Ltd, 2010; (b) H. Yang, CN 105985367, EverDisplay Optronics
(Shanghai) Limited, 2016.
7
a catalytic reaction: (b) L. D. Curless and M. J. Ingleson, Organome- 20 J. T. Reeves, D. R. Fandrick, Z. Tan, J. J. Song, H. Lee, N. K. Yee and
tallics, 2014, 33, 7241. C. H. Senanayake, Org. Lett., 2015, 14, 4388.
13306 | Chem. Commun., 2019, 55, 13303--13306
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