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

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.