Preparation of indenes used as intermediate in synthesis of active compounds involves reacting aliphatic organometallic compounds with transition metal catalyst

摘要

Indenes are prepared from indenes of 4-choro-2-alkylindenes are prepared by reacting aliphatic organometallic compounds with a transition metal catalyst. Preparation of indenes of the formula (II) from indenes of 4-chloro-2-alkylindenes of formula (I) by reaction with aliphatic organometallic compounds of formulae (III) in the presence of a transition metal catalyst. X1 = Cl; Y1 = 1-40C, e.g. (fluorinated) 1-25C alkyl, 2-25alkenyl, 2-25C-alkynyl, 3-15C-alkylalkenyl, 3-15C-alkylalkynyl, (fluorinated) 6-24C-aryl, 4-24C-heteroaryl, 5-24C-alkylheteroaryl, (fluorinated) 7-30C-arylalkyl, (fluorinated) 7-30C-alkylaryl, 1-12C-alkoxy, 6-24C-aryloxy, fluorine atom or heteroatom-containing groups, e.g. boron-, silicon-, nitrogen-, oxygen- or sulfur, containing groups, which may bear substituents; Y2 = 1-40C groups, e.g. (fluorinated) 1-25C-alkyl, 2-25C-alkenyl, 2-25C-alkynyl, 3-15C alkylalkenyl, 3-l5C-alkylalkynyl, (fluorinated) 6-24C-aryl, 4-24C-heteroaryl, 5-24C-alkylheteroaryl, (fluorinated) 7-30C-arylalkyl, (fluorinated) 7-30C-alkylaryl, 1-l2C-alkoxy, 6-24C-aryloxy or heteroatom-containing groups, e.g. boron-, silicon-, nitrogen-, oxygen- or sulfur-containing groups, which maybe bear substituent(s); R1 = cyclic aliphatic hydrocarbon groups, e.g. 1-25C-alkyl which may in turn bear a substituents, and groups bound via an aliphatic group to the indenyl skeleton, e.g. 3-15C-alkenylalkyl, 3-15C-alkynylalkyl, 5-24C-heteroarylalkyl, 7-30C-arylalkyl, 2-30C-alkyloxyalkyl, 7-30C-aryloxyalkyl, 8-30-alkylarylalkyl or other heteroatom-containing groups which are bound via an aliphatic group to the indenyl skeleton, e.g. boron-, silicon-, nitrogen-, oxygen- or sulfur-containing groups and may bear substituents; M1 = element of group 1, 2, 12, 13 or 14 of the Periodic Table of the elements; X2 = halogen atoms, hydroxy group, alkoxy groups, aryloxy groups, mesylate, tosylate or triflate; m = 0-3; n = 1-4; p = 0-4; q = 1-4; r = 1, 2 or 3; t = 0, 1 or 2. Groups Y1 and Y2 may also together form a cyclic aliphatic or aromatic ring system which may in turn be substituted and may contain heteroatoms. An Independent claim is also included for an indene of formulae (IIa) or (IIb). R2 = 1-10C alkyl; R3 = monocyclic or polycyclic 5-15C alkyl or CH2R4; R4 = 6-14C aryl, 7-15C alkylaryl or monocyclic or polycyclic 5-15C alkyl.