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A synthesis of fused thieno[3,2-d]thiazoles via direct functionalization of C(sp3)-H bonds in acetophenones was reported. The transformation is divergent to afford either 2-phenylbenzo[4,5]thieno[3,2-d]thiazoles or benzo[4,5]thieno[3,2-d]thiazol-2-yl(phenyl)methanones. Cross-coupling of acetophenones with C-H… Click to show full abstract
A synthesis of fused thieno[3,2-d]thiazoles via direct functionalization of C(sp3)-H bonds in acetophenones was reported. The transformation is divergent to afford either 2-phenylbenzo[4,5]thieno[3,2-d]thiazoles or benzo[4,5]thieno[3,2-d]thiazol-2-yl(phenyl)methanones. Cross-coupling of acetophenones with C-H bonds in phenylacetic acids, methylazaarenes, and aldehydes was also feasible. Excellent tolerance of functionalities was observed. Our method marks a rare functionalization of C(sp3)-H bonds in acetophenones to obtain heterocycles in the absence of prefunctionalized oxime esters.
Journal Title: Organic letters
Year Published: 2019
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