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This research explores a ruthenium-catalyzed approach for sulfur-directed ortho-functionalization of benzyl thioethers and the cleavage of C–Se bonds.

April 8, 2026

Ru(II)‐Catalyzed Sulfur‐Directed Ortho ‐C–H Functionalization: Divergent Reactivity and C–Se Bond Cleavage With Maleimides

Key Points

This research explores a ruthenium-catalyzed approach for sulfur-directed ortho-functionalization of benzyl thioethers and the cleavage of C–Se bonds.
Utilized ruthenium catalysis for ortho-C–H functionalization of benzyl thioethers.
Examined effects of temperature and additives like Cu(OAc)2 and Zn(OAc)2 on product selectivity.
Investigated reactions of benzyl phenyl selenoethers to form selenated maleimide derivatives.
Identified divergent reaction pathways based on temperature and additives used.
Observed that Cu(OAc)2 favors thermally sensitive ortho-alkenylation.
Discovered that Zn(OAc)2 leads to exclusive ortho-alkylation products.
Confirmed C─Se bond cleavage in reactions with benzyl phenyl selenoethers.

Abstract

Sulfur-directed, selective ortho-functionalization of benzyl thioethers with maleimides has been achieved under a ruthenium-catalyzed system; herein, temperature and additive play a crucial role in determining product selectivity. The ortho-alkenylated maleimide proved thermally sensitive in the presence of Cu(OAc)2, whereas the presence of Zn(OAc)2 diverted the reaction pathway towards an exclusive ortho-alkylation. However, benzyl phenyl selenoethers afford selenated maleimide derivatives via C─Se bond cleavage under established reaction protocols.

Ru(II)‐Catalyzed Sulfur‐Directed Ortho ‐C–H Functionalization: Divergent Reactivity and C–Se Bond Cleavage With Maleimides

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Abstract

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