Advances in Cu and Ni-catalyzed Chan–Lam-type coupling: synthesis of diarylchalcogenides, Ar₂–X (X = S, Se, Te)

Abstract

Organochalcogenides are important class of compounds encountered in organic synthesis, chemical biology and materials chemistry. The development of Ar2-S/Se/Te bond formation, mostly in the synthesis of diarylchalcogenides has garnered considerable...

Transition‐Metal‐Free C−S, C−Se, and C−Te Bond Formation from Organoboron Compounds

“…[24] Chan-Lam-type coupling is a valuable procedure to prepare these chalcogenides from suitable and stable borates and boronic acids as substrates. [25] To demonstrate the importance of synthesis of diorganyl chalcogenides, some reviews were described. As example, Fernandes and co-workers, [25] in 2020 described the advances of Cu and Ni-catalyzed Chan-Lam-type coupling.…”

“…Traditional protocols are transition‐metal‐mediated cross‐coupling reactions between different chalcogen sources, including chalcogenyl halides, diorganyl dichalcogenides, elemental chalcogen and chalcogenols with aryl halides, [21] aryldiazonium salts, [22] aryl stannanes [23] and epoxides [24] . Chan‐Lam‐type coupling is a valuable procedure to prepare these chalcogenides from suitable and stable borates and boronic acids as substrates [25] …”

“…To demonstrate the importance of synthesis of diorganyl chalcogenides, some reviews were described. As example, Fernandes and co‐workers, [25] in 2020 described the advances of Cu and Ni‐catalyzed Chan‐Lam‐type coupling. In the same year, Dong and co‐workers [5g] related the latest progress in transitions metal catalyzed Chan‐Lam coupling reaction to form various C‐heteroatom (N, O, P, S and Se) or C‐C bonds.…”

Synthesis of Organosulfur and Related Heterocycles under Mechanochemical Conditions

“…Among them, transition-metal (such as Pd, Ir, Rh, Au, Ag, In, and Fe)-catalyzed cross-coupling reaction between organic halides and R 2 X 2 or RXH (X = S, Se, and Te) is perhaps the most widely employed approach. Another strategy that has also been employed widely for the synthesis of organochalcogenide is transition-metal (Cu and Ni)-catalyzed Chan-Lam-type coupling between organoboronic acids and various S, Se, and Te sources such as R 2 X 2 or RXH (X = S, Se, and Te) . Despite significant advancement, these methods suffer from at least one or more of the following severe limitations: Requirement of an expensive and toxic transition metal catalyst Requirement of expensive and hazardous ligand Requirement of hazardous and high boiling organic solvents Requirement of harsh reaction conditions including high temperature …”

“…Another strategy that has also been employed widely for the synthesis of organochalcogenide is transition-metal (Cu and Ni)-catalyzed Chan-Lam-type coupling between organoboronic acids and various S, Se, and Te sources such as R 2 X 2 or RXH (X = S, Se, and Te). 13 Despite significant advancement, these methods suffer from at least one or more of the following severe limitations: (a) Requirement of an expensive and toxic transition metal catalyst (b) Requirement of expensive and hazardous ligand (c) Requirement of hazardous and high boiling organic solvents (d) Requirement of harsh reaction conditions including high temperature However, in the context of green synthesis, the development of methodologies for the synthesis of organochalcogenides, in particular, organosulfides and related heterocycles without using hazardous/toxic transition-metal catalyst, ligand, and solvent is always desirable. In the past decade, ball-milling has received significant attention as a "green synthetic tool" in conducting various useful organic transformations with efficacy and more often without using an organic solvent.…”