A novel silicon-based linkage and cleavage strategy for solid-phase synthesis: Formation of resin-linked zwitterionic pentacoordinate silicates as the key step and release of the target molecules in a traceless fashion
R. Tacke et al., A novel silicon-based linkage and cleavage strategy for solid-phase synthesis: Formation of resin-linked zwitterionic pentacoordinate silicates as the key step and release of the target molecules in a traceless fashion, ORGANOMETAL, 19(25), 2000, pp. 5297-5309
A novel silicon-based linkage and cleavage strategy for solid-phase synthes
is of aromatic organic compounds has been developed. The method is based on
the following steps: (i) attachment of silanes of the formula type (RR2)-R
-1(R3O)Si(CH2)(n)NCH2CH2N(R-4)CH2CH2 (R-1 = aryl; R-2 = aryl, alkyl; R-3, R
-4 = alkyl; n = 1, 3) to a Merrifield resin via R-4, (ii) reactions with th
e resin-linked silanes (chemical, transformations of the aryl group R-1; R-
1 --> --> --> R-1*), and (iii) treatment of the R-1*R-2((RO)-O-3)Si(CH2)(n)
NCH2CH2N(R-4)CH2CH2-co resin with 1,2-dihydroxybenzene in acetonitrile at 5
0 degreesC to give the cleavage products R-1*H (release of the target molec
ules in a traceless fashion), (RH)-H-2, and (ROH)-O-3, along with the resin
-linked zwitterionic pentacoordinate silicate of the formula type (1,2-C6H4
O2)(2)Si(CH2)(n)N(H)CH2CH2N(R-4)CH2CH2.