Abstract
(I)A palladium- and ligand-free reaction condition for Sonogashira-type coupling was developed, which used CuCl2 as the catalyst system and was applicable to one-pot three-steps synthesis of benzo[b]thiophene derivatives. Since this catalyst is cheap and easily removable (by washing), it may have some practical usage for chemists. (II)Total synthesis of raloxifene was accomplished in seven steps in 21% of total yields. This novel route was starting from the corresponding thioanisole 55. The iodination of compound 55 by treating with NIS in the presence of TMSCl can provide the 46% yield of the desired iodothioanisole 56. After the CuCl2-promoted one-pot three-step protocol was employed to iodothioanisole 56 as the key step for the construction of benzo[b]thiophene skeleton 58, the further three steps were carried out via Grignard reagent addition, deprotection, and SNAr reaction to afford the raloxifene 62.
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