Method for allylating and vinylating aryl, heteroaryl, alkyl, and alkene halogenides using transition metal catalysis

A process for preparing organic compounds of the general formula (I)

• R—R′ (I)
• in which
• R is an optionally mono- or polysubstituted aryl, heteroaryl, alkenyl or alkyl radical, and
• R′ is an optionally substituted vinyl radical or ally radical, and
• the process comprises:
• converting a compound of the general formula (II)
• R—X (II)
• in which
• X is fluorine, chlorine, bromine or iodine, and
• R is as defined for formula (I),
• to an organomagnesium compound of the general formula (III)
• [M+]n[RmMgXkYl] (III)
• in which
• R is as defined for formula (I),
• X is an anion as defined for formula (II),
• M is a monovalent cation,
• Y is a monovalent anion,
• n is either 0 or n is 1, 2, 3, 4,
• m is 1, 2, 3, 4, 5 or 6,
• k is 0, 1, 2, 3 or 4,
• l is 0, 1, 2, 3 or 4, and
• n+2=m+k+l, and
• reacting the organomagnesium compound (III) with a compound of the general formula (IV)
• in which
• R′ is as defined for formula (I) and is bonded to the oxygen atom in the allyl or vinyl position, and
• R″ is an optionally substituted alkyl, alkoxy, aryl, aryloxy, heteroaryl or heteroaryloxy group,
• to produce the compound of the general formula (I);
• wherein the process comprises converting compound (II) to compound (III) in the presence of
• a) catalytic amounts of an iron compound, based on the compound of the general formula (II),
• b) the compound of general formula (IV), and optionally
• c) a nitrogen-, oxygen- and/or phosphorus-containing additive in a catalytic or stoichiometric amount, based on the compound of the general formula (II);
• wherein, after formation of the organomagnesium compound (III), the organomagnesium compound (III) reacts further in situ with the compound of the general formula (IV) to produce the compound of the general formula (I).