In the present review, we discuss recent progress in the field of C-Z bond formation reactions (Z = S, Se, Te) catalyzed by transition metals. Two complementary methodologies are considered─catalytic cross-coupling reactions and catalytic addition reactions. The development of advanced catalytic systems is aimed at improved catalyst efficiency, reduced catalyst loading, better cost efficiency, environmental concerns, and higher selectivity and yields. The important rise of research efforts in sustainability and green chemistry areas is critically assessed. The paramount role of mechanistic studies in the development of a new generation of catalytic systems is addressed, and the key achievements, problems, and challenges are summarized for this field.

Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges.

A practical approach for the regioselective synthesis of 3-arylthioindoles has been accomplished using a combination of 1-aryltriazene/CS2 as a new sulfenylation source. The methodology employs molecular iodine as a catalyst and is compatible with a variety of structurally diverse reactants.

Iodine-Catalyzed Synthesis of 3-Arylthioindoles Employing a 1-Aryltriazene/CS2 Combination as a New Sulfenylation Source.

Palladium‐Catalyzed Picolinamide‐Directed Benzylic C(sp3)−H Chalcogenation with Diaryl Disulfides and Diphenyl Diselenide

Organoselenium compounds find versatile applications in organic synthesis, materials synthesis, and ligand chemistry. Organoselenium heterocycles are widely studied agents with diverse applications in various biological processes. This review highlights the recent progress in the synthesis of selenium heterocycles using diorganyl diselenides with keen attention on green synthetic approaches, scopes, C–H selanylation, the mechanisms of different reactions and insights into the formation of metal complexes. The C–H selanylation using diorganyl diselenides with different catalysts, bases, transition metals, iodine salts, NIS, hypervalent iodine, and other reagents is summarised. Finally, the diverse binding modes of bis(2/4-pyridyl)diselenide with different metal complexes are also summarised.

Janylson Souza Araújo

Papers

Fe(III)-Catalyzed direct C3 chalcogenylation of indole: The effect of iodide ions