Useful Silyl Compound
Silyl compound 1 reacts with iodobenzene diacetate in the presence of trifluoromethanesulfonic acid to give hypervalent iodine compound 2. Treatment of compound 2 with tetrabutylammonium fluoride at room temperature generates benzyne 3, which in turn give several types of cyclic compounds in the presence of a trapping agent such as furan.1) Since the generation of 3 from 1 is carried out under mild conditions, this methodology can be utilized in various fields.
The reaction of 1 with 1,2-bis(trichlorotelluro)benzene can also provide telluranthene 4.2)
References
- 1)A new and efficient precursor of benzyne
- T. Kitamura, M. Yamane, J. Chem. Soc., Chem. Commun. 1995, 983.
- T. Kitamura, M. Yamane, K. Inoue, M. Todaka, N. Fukatsu, Z. Meng, Y. Fujiwara, J. Am. Chem. Soc. 1999, 121, 11674.
- 2)A new approach to the synthesis of telluranthene
- B. B. Rivkin, I. D. Sadekov, P. I. Gadzhieva, V. I. Minkin, Chem. Heterocycl. Compd. 1991, 1149.
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