Abstract
A new non-photochemical synthesis of disubstituted heterohelicene is described. The directed metalation at the 1-position of 2-(4,4-dimethyloxazolin-2-yl)-7-methylbenzo[1,2-b:4,3-b′]dithiophene was accomplished by the use of BuLi in ether to give the organolithium species which, upon treatment with iodine and chlorotributyltin, gave 2-(4,4-dimethyloxazolin-2-yl)-1-iodo-7-methylbenzo[1,2-b:4,3-b′]-dithiophene and 2-(4,4-dimethyloxazolin-2-yl)-7-methyl-1-tributylstannylbenzo-[1,2-b:4,3-b′]dithiophene in high yields. Palladium-catalyzed cross-coupling between them, followed by the intramolecular McMurry coupling reaction, gave 2,13-dimethyl[7]thiaheterohelicene in good yield.
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