Transition-metal-free n-arylation of tertiary amines using arynes

A transition metal-free synthesis of tertiary arylamines compounds of general formula (I)

• wherein
• R1=ethyl, methyl or;
• R2=H, alkyl (C1-C5), aryl (phenyl, C6-C8), halogen (F, Cl, Br, I), esters (C2-C4), CHO, CN, OH, CH═CH—COOEt, CH═CH—C6H4NO2, OCH3, OPh,
• R3=H, CH3, halogen (F, Cl, Br, I),
• R4=H or D;
• or R2+R3=—O—CH2-O—, —CH═CH—CH═CH—;
• —C(SO2Cl)═CH—CH═CH—;
• comprising the steps of:
• ii. mixing 2-trimethylsilylaryl trifluoromethyl sulphonate of formula (II) and tertiary amine compounds of formula (III) in the ratio ranging between 2:1 to 1:2 in presence of 18-crown-6, KF and solvent (THF)
• wherein R1, R2 and R3 is as defined above.