Catalytic Synthesis of π-Conjugated Silole through Si–C (sp3) Bond Activation

Qing-Wei Zhang; Kun An; Wei He

doi:10.1055/s-0034-1380458

Synlett, Inhaltsverzeichnis

Synlett 2015; 26(09): 1145-1152
DOI: 10.1055/s-0034-1380458

synpacts

Catalytic Synthesis of π-Conjugated Silole through Si–C (sp³) Bond Activation

Autor*innen

Qing-Wei Zhang

School of Medicine and Tsinghua-Peking Joint Centers for Life Science, Tsinghua University, Beijing 100084, P. R. of China eMail: whe@mail.tsinghua.edu.cn
Kun An

School of Medicine and Tsinghua-Peking Joint Centers for Life Science, Tsinghua University, Beijing 100084, P. R. of China eMail: whe@mail.tsinghua.edu.cn
Wei He*

School of Medicine and Tsinghua-Peking Joint Centers for Life Science, Tsinghua University, Beijing 100084, P. R. of China eMail: whe@mail.tsinghua.edu.cn

Abstract

Alle Artikel dieser Rubrik

Abstract

Conjugated siloles represent an important class of photoluminescence material. Traditional synthesis of siloles often suffered from low functional group compatibility due to the usage of stoichiometric organic lithium or magnesium reagents. In the past years, catalytic Si–C bond activation has emerged as a new strategy for the synthesis of siloles. For the benefit of this fast-developing research area, this article highlights the related pioneering work as well as our recent discovery of a tandem cyclization/Si–C (sp³) activation reaction that enables the rapid synthesis of indole- and benzofuran-conjugated siloles. We also discuss the reaction mechanism in greater detail.

Key words

silicon - rhodium - tandem reactions - metalation - chemoselectivity

Volltext

Referenzen

References and Notes

1a Yamaguchi S, Tamao K In Silicon-Containing Polymers: The Science and Technology of their Synthesis and Applications . Jones RG, Ando W, Chojnowski J. Kluwer Academic Publishers; Dordrecht: 2000: 461-498
1b Corey JY In Adv. Organomet. Chem. . Anthony FH, Mark JF. Academic Press; New York: 2011: 1-328
1c Ojima I In The Chemistry of Organic Silicon Compounds . Patai S, Rappoport Z. Wiley-Interscience; Chichester: 1989: 1479

2a Shimizu M, Mochida K, Katoh M, Hiyama T. J. Phys. Chem. C 2010; 114: 10004
2b Shimizu M, Mochida K, Hiyama T. J. Phys. Chem. C 2011; 115: 11265
2c Shimizu M, Mochida K, Hiyama T. Angew. Chem. Int. Ed. 2008; 47: 9760
2d Geramita K, McBee J, Shen Y, Radu N, Tilley TD. Chem. Mater. 2006; 18: 3261
2e Pusztai E, Toulokhonova IS, Temple N, Albright H, Zakai UI, Guo S, Guzei IA, Hu R, West R. Organometallics 2013; 32: 2529
2f Li Z, Dong YQ, Lam JW. Y, Sun J, Qin A, Häußler M, Dong YP, Sung HH. Y, Williams ID, Kwok HS, Tang BZ. Adv. Funct. Mater. 2009; 19: 905

3a Toal SJ, Jones KA, Magde D, Trogler WC. J. Am. Chem. Soc. 2005; 127: 11661
3b Toal SJ, Magde D, Trogler WC. Chem. Commun. 2005; 5465
3c Carroll JB, Braddock-Wilking J. Organometallics 2013; 32: 1905

4 Lu G, Usta H, Risko C, Wang L, Facchetti A, Ratner MA, Marks TJ. J. Am. Chem. Soc. 2008; 130: 7670

5a Chen J, Cao Y. Macromol. Rapid Commun. 2007; 28: 1714
5b Coffin RC, Peet J, Rogers J, Bazan GC. Nat. Chem. 2009; 1: 657
5c Hou J, Chen HY, Zhang S, Li G, Yang Y. J. Am. Chem. Soc. 2008; 130: 16144
5d Chu TY, Lu J, Beaupre S, Zhang Y, Pouliot JR, Wakim S, Zhou J, Leclerc M, Li Z, Ding J, Tao Y. J. Am. Chem. Soc. 2011; 133: 4250

6a Zhan X, Barlow S, Marder SR. Chem. Commun. 2009; 1948
6b Yamaguchi S, Goto T, Tamao K. Angew. Chem. Int. Ed. 2000; 39: 1695
6c Tamao K, Yamaguchi S, Shiro M. J. Am. Chem. Soc. 1994; 116: 11715

7 Corey JY, Chang LS. J. Organomet. Chem. 1986; 307: 7

8a Mochida K, Shimizu M, Hiyama T. J. Am. Chem. Soc. 2009; 131: 8350
8b Shintani R, Otomo H, Ota K, Hayashi T. J. Am. Chem. Soc. 2012; 134: 7305

9a Furukawa S, Kobayashi J, Kawashima T. J. Am. Chem. Soc. 2009; 131: 14192
9b Yabusaki Y, Ohshima N, Kondo H, Kusamoto T, Yamanoi Y, Nishihara H. Chem. Eur. J. 2010; 16: 5581
9c Kuninobu Y, Yamauchi K, Tamura N, Seiki T, Takai K. Angew. Chem. Int. Ed. 2013; 52: 1520

10a Tobisu M, Onoe M, Kita Y, Chatani N. J. Am. Chem. Soc. 2009; 131: 7506
10b Onoe M, Baba K, Kim Y, Kita Y, Tobisu M, Chatani N. J. Am. Chem. Soc. 2012; 134: 19477

11a Wang L, Duan Z. Chin. Sci. Bull. 2012; 58: 307
11b Shirakawa E, Masui S, Narui R, Watabe R, Ikeda D, Hayashi T. Chem. Commun. 2011; 47: 9714
11c Ojima I, Fracchiolla DA, Donovan RJ, Banerji P. J. Org. Chem. 1994; 59: 7594
11d Wang C, Luo Q, Sun H, Guo X, Xi Z. J. Am. Chem. Soc. 2007; 129: 3094
11e Liang Y, Geng W, Wei J, Ouyang K, Xi Z. Org. Biomol. Chem. 2012; 10: 1537

12a Nakao Y, Hiyama T. Chem. Soc. Rev. 2011; 40: 4893
12b Seiser T, Cramer N. Angew. Chem. Int. Ed. 2010; 49: 10163
12c Shindo M, Matsumoto K, Shishido K. Angew. Chem. Int. Ed. 2004; 43: 104
12d Rauf W, Brown JM. Angew. Chem. Int. Ed. 2008; 47: 4228

13a Liang Y, Zhang S, Xi Z. J. Am. Chem. Soc. 2011; 133: 9204
13b Liang Y, Geng W, Wei J, Xi Z. Angew. Chem. Int. Ed. 2012; 51: 1934
13c Meng T, Ouyang K, Xi Z. RSC Advances 2013; 3: 14273

14a Isono N, Lautens M. Org. Lett. 2009; 11: 1329
14b Shu D, Song W, Li X, Tang W. Angew. Chem. Int. Ed. 2013; 52: 3237
14c Li X, Song W, Tang W. J. Am. Chem. Soc. 2013; 135: 16797
14d Yao B, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2012; 51: 12311

15 Müller TE, Hultzsch KC, Yus M, Foubelo F, Tada M. Chem. Rev. 2008; 108: 3795

16a So CM, Kume S, Hayashi T. J. Am. Chem. Soc. 2013; 135: 10990
16b Davidson PJ, Lappert MF, Pearce R. Acc. Chem. Res. 1974; 7: 209

17 Crystallographic data have been deposited at the Cambridge Crystallographic Data Centre as CCDC-948123 (2m) and 979513 (3b). Copies of the data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif.
18 Chen X.-K, Zou L.-Y, Ren A.-M, Fan J.-X. Phys. Chem. Chem. Phys. 2011; 13: 19490

19a Yu Z, Lan Y. J. Org. Chem. 2013; 78: 11501
19b Chen WJ, Lin ZY. Dalton Trans. 2014; 43: 11138

20 Barder TE, Walker SD, Martinelli JR, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 4685