Method for the organometallic production of organic intermediate products comprising carbon-heteroatom bonds achieved by the deprotonation of heteroatoms

1 . A process for forming heteroatom-carbon bonds, said process comprising reacting in a reaction mixture aliphatic or aromatic halogen compounds (I) with lithium metal to generate a lithium compound (II), deprotonating the compounds (III) or (V) by reaction with the lithium compound (II), and reacting the resulting lithium salts of the formula (IV) or (VI) with a suitable carbon electrophile to form the heteroatom-carbon bond and produce the product (VIII) or (VIII) (equation 1).

Step 1: Generation of the base

Step 2: Deprotonation of the substrate

Step 3: Reaction with an electrophile

where, R is methyl, a primary, secondary or tertiary branched or unbranched alkyl radical having from 1 to 20 carbon atoms, a phenyl, aryl or heteroaryl radical, alkyl substituted by a radical selected from the group consisting of methyl, primary, secondary or tertiary alkyl, phenyl, substituted phenyl, aryl, heteroaryl, alkoxy, dialkylamino, alkylthio, substituted or unsubstituted cycloalkyl having from 3 to 8 carbon atoms, and mixtures thereof;

Hal is a halogen selected from the group consisting of fluorine, chlorine, bromine, iodine, and mixtures thereof,

X 1 is an oxygen or sulfur bound via a single bond to R1 or an sp2-hybridized nitrogen bound via a double bond to R1, and X 2 is an sp3-hybridized nitrogen;

the radicals R 1 and R 2 are independently of one another substituents selected from the group consisting of hydrogen, methyl, primary, secondary or tertiary, cyclic or acyclic alkyl, alkenyl or alkynyl radicals having from 1 to 20 carbon atoms, substituted cyclic or acyclic alkyl groups, acyl groups, alkoxy, aryloxy, dialkylamino, alkylamino, arylamino, diarylamino, alkylarylamino, imino, sulfone, sulfonyl, phenyl, substituted phenyl, alkylthio, diarylphosphino, dialkylphosphino, alkylarylphosphino, dialkylaminocarbonyl or diarylaminocarbonyl, monoalkylaminocarbonyl or monoarylaminocarbonyl, alkylarylaminocarbonyl, alkoxyalkyl, carboxylate, alkylcarboxylate, CN, CHO, heteroaryl and mixtures thereof, where two adjacent radicals R 1 and R 2 can together correspond to an aromatic or aliphatic ring.

2 . The process as claimed in claim 1 , wherein the compounds of the formula (III) are selected from the group consisting of alcohols, thiols, phenols, thiophenols, oximes, hydrazones, and mixtures thereof, and the compounds of the formula (V) are selected from the group consisting of amines, carboxamides, sulfonamides, hydrazines, and mixtures thereof.

3 . The process of claim 1 , wherein the electrophile is selected from the group consisting of aryl or alkyl cyanates, isocyanates, oxirane, substituted oxiranes, aziridines, substituted aciridines, imines, aldehydes, ketones, organic halogen compounds, triflates, other sulfonates, sulfates, ketenes, carboxylic acid chlorides, carboxylic esters, thioesters and amides, carbonic esters, phosgene derivatives, and mixtures thereof.

4 . The process of claim 1 , wherein the reaction is carried out in an organic ether solvent.

5 . The process of claim 1 , wherein said reacting step is carried out at a reaction temperature in the range from −100 to +70° C.

6 . The process of claim 1 , wherein a concentration of aliphatic or aromatic intermediates of the formula (II) are in the range from 5 to 30% by weight.

7 . The process of claim 1 , wherein lithium metal is added in an amount per mole of halogen reacted ranging from 1.95 to 2.5 mol.

8 . The process of claim 1 , further comprising adding organic redox systems to the reaction mixture.