Indole‐ and Benzofuran‐Thioglycoside Synthesis via Palladium‐Catalyzed Migita/Larock Couplings: Synthesis and Photophysical Investigations

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An efficient catalytic approach for the synthesis of novel indole‐ and benzofuran‐thioglycoside derivatives by using simple cross‐coupling reactions is established. The strategy involves two Pd‐catalyzed cross‐couplings including C─S bond‐forming reaction between glycosyl thiols and p ‐iodoalkyne, followed by a Larock reaction. Following this catalytic approach, various indole‐ and benzofuran‐containing thioglycoside derivatives were prepared with moderate to good yields (54%–84%). Among all thioglycoside derivatives synthesized, the fully acetylated N ‐Ts indole‐derivative exhibits cytotoxicity against the human colon cancer cell line (HCT116) with an IC 50 at the micromolecular level (6.94 ± 0.94 μM). Furthermore, the photophysical properties of all thioglycoside derivatives are studied.