New Routes to 1,2- and 1,3-Bis(silyl)indoles-Synthesis of the first Bis(indol-3-yl)silane

Author： Frenzel A. Herbst-Irmer R. Klingebiel U. Noltemeyer M. Rudolph S.

ISSN： 1024-1221

Source： Main Group Chemistry, Vol.1, Iss.4, 1996-10, pp. : 399-408

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Abstract

New ways to synthesize 1,2- and 1,3-bis(silyl)indoles are shown in this paper and new members of these classes of substances are isolated and characterized The crystal structures of the lithium salt of 2-(tert-butyldimethylsilyl) indole (1) (space group P2 1 /c,a = 1018.0(3), b = 1651.4(3), c = 1648.9(5) pm, β = 94.54(3)°, V = 2.763(1) nm 3 , &rgr;calc = 1.090 Mg/m 3 , Z = 4, 4831 reflections, R1 (I > 2&sgr;(I) = 0.052, wR2 (all data) = 0.152) and 1-(di-tert-butylfluorosilyl)-2-(trimethylsilyl)indole(4) (space group P2 1 /c,a = 1015.5(1), b = 1733.5(3), c = 1261.3(2)pm, β = 105.61(2)°, V = 2.1385(5) nm 3 , &rgr;calc = 1.086 Mg/m 3 , Z = 4, 2779 reflections, R1 (I > 2&sgr;(I) = 0.055, wR2 (all data) = 0.163) are reported. Furthermore the first examples of bis(indol-3-yl)silanes (9, 10) are isolated. Specific reactions for the desilylation of 1, 3-bis(silyl)indoles are discussed.