Process for the preparation of ring compounds

A process for the preparation of a ring compound of formulae I to IV

• where
• m and n, independently of one another, are identical or different and are 0 or 1, but the sum (m+n) is 1 or 2,
• X is a single bond,
• L, independently of one another, are identical or different and are R, F, Cl, Br, I, OH, OR, SH, SR, CN, NO2, NO, CHO, COOH, COOR, CONH2, CONHR, CONR2, CF3, NH2, NHR or NR2,
• R is an alkyl, alkenyl or acyl group having from up to 12 carbon atoms, or an aryl group having 6 carbon atoms, which is optionally substituted by an alkyl group having from 1 to 12 carbon atoms, and,
• a, b, c, d, e and f, independently of one another, are identical or different and are 0, 1 or 2, and the sum (a+b+c+d+e+f)=1 to 8,
• one or two CH groups in the aromatic ring systems of the formulae I to IV may be replaced by N,
• R1 and R2, independently of one another, are identical or different and are H, F, Cl, CN, NCS, a straight-chain or branched, optionally chiral alkyl radical or alkoxy radical having from 1 to 12 carbon atoms or an alkenyl radical or alkynyl radical having from 2 to 8 carbon atoms, in each of which, in addition, one CH2 group may be replaced by —O—, —CO—, —O—CO— or —COO— in such a way that heteroatoms are not linked directly to one another and/or one or more H may be replaced by halogen, and
• in the case where m=0 in R1 or n=0 in R2, one CH2 group in R1 or R2 may be replaced by one of the following groups:
• a) trans-1,4-cyclohexylene, in which, in addition, one or more non-adjacent CH2 groups may be replaced by —O— and/or —S—,
• b) a radical from the group consisting of 1,4-bicyclo[2.2.2]octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl, or
• c) 1,4-cyclohexenylene,
• and in which the radicals a), b) and c) may also be substituted by CN and/or halogen,
• said process comprising:
• preparing a ring compound of formulae I to IV, via combinatorial synthesis, starting from a compound of formulae V to VIII
• where
• Z is I, Cl, Br or triflate,
• M is Si, Ge or Sn, and
• R3, R4
• and R5, independently of one another, are identical or different and are H, C1–C12-alkyl or C1–C12-alkoxy,
• in which the following reaction steps are carried out in a matrix-like arrangement of reaction vessels:
• A) Suzuki coupling with a boronic acid or a boronic acid ester of formula X
• where
• R6 and R7, independently of one another, are identical or different and are H, C1–C12-alkyl, C2–C12-alkenyl or aryl, and where R6 and R7 may also be bridged in a cyclic manner,
• B) subsequent halo-demetallation, and
• C) Suzuki coupling with a boronic acid or a boronic acid ester of
• where one or two CH groups in the aromatic ring systems of formulae V to VIII and X and XI may also be replaced by N.