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US 10,351,492 B2Granted
Introduction of alkyl substituents to aromatic compounds
AssigneeB. G. Negev Technologies and Applications Ltd.
InventorsDoron Pappo, Regev Parnes
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Abstract
Novel selective synthesis route to introduce primary alkyl groups on aromatic compounds is disclosed. The synthesis route is based on electrophilic aromatic substitutions of thionium ion species that are generated in-situ from aldehydes and thiols, affording benzyl sulfide that can be reduced with triethylsilane.
Claims8
A process comprising:
- reacting a compound having Formula II:
- with a compound having Formula III:
- and with R3SH
- in the presence of an acidic catalyst and a suitable solvent,
- thereby forming a compound having Formula I:
- wherein:
- R1 is (C)n or aryl, wherein n is between 1 to 20;
- R2 represents 0 to 5 substituents, wherein, in each occurrence, each substituent is independently selected from the group consisting of:
- alkyl, alkenyl, alkynyl, cycloalkyl, heteroalicyclic, aryl, heteroaryl, hydroxy, alkoxy, aryloxy, thiohydroxy, thioalkoxy, thioaryloxy, halide, amine, amide, carbonyl, thiocarbonyl, carboxy, thiocarboxy, epoxide, sulfonate, sulfonyl, sulfinyl, sulfonamide, nitro, nitrile, isonitrile, thiirane, aziridine, nitroso, hydrazine, sulfate, azide, phosphonyl, phosphinyl, urea, thiourea, carbamyl and thiocarbamyl, or the substituents are joined together so as to form a fused ring system containing up to three 6-member carbocyclic, each being substituted or non-substituted;
- R3 is selected from alkyl, aryl, alkoxy, aryloxy, carbonyl, carboxy, substituted or non-substituted;
- and
- R4, R5, and R6 are each independently selected from the group consisting of:
- hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heteroalicyclic, aryl, heteroaryl, hydroxy, alkoxy, aryloxy, thiohydroxy, thioalkoxy, thioaryloxy, halide, amine, amide, carbonyl, thiocarbonyl, carboxy, thiocarboxy, epoxide, sulfonate, sulfonyl, sulfinyl, sulfonamide, nitro, nitrile, isonitrile, thiirane, aziridine, nitroso, hydrazine, sulfate, azide, phosphonyl, phosphinyl, urea, thiourea, carbamyl and thiocarbamyl,
- the process further comprising a subsequent step of reacting said compound having Formula I with a reducing agent, thereby forming the compound having Formula IV:
11 more elements
Dependencies are inferred from the claim text.