Recent advances in copper-catalyzed C-S cross-coupling reactions

Abstract

Copper-catalyzed cross-coupling reactions offer a powerful tool for the formation of carbonheteroatom bonds. Copper catalysis has an indisputable advantage over the other catalytic systems due to its low cost and the use of readily accessible and stable ligands. Among the various copper-catalyzed coupling reactions, C-S bond forming reactions have gained much attention due to its applications in the synthesis of molecules having biological and pharmaceutical impact. This review illustrates the current strategies and applications of Cucatalyzed C-S cross coupling reactions.

Environmentally Friendly and Recyclable CuCl2-Mediated C–S Bond Coupling Strategy Using DMEDA as Ligand, Base, and Solvent

“…5 Earlier studies on C–S bond cross-coupling reactions required stoichiometric amounts of metal catalyst, high reaction temperatures, and toxic or high boiling point solvents and etc. 6 To overcome these drawbacks, Migita-like transition-metal­-catalyzed C–S bond cross-coupling reactions, such as palladium, 7 rhodium, 8 cobalt, 9 nickel, 10 copper, 5b 11 and iron, 12 as well as ligated-metal complexes, 13 were developed and some great successes have been achieved. 14 Among the transition-metal-catalyzed reactions, copper-catalyzed (C–C, C–N, C–O, C–S, etc.)…”

Nickel(II)‐Mediated C−S Cross‐Coupling Between Thiols and ortho‐Substituted Arylboronic Acid

“…Numerous reactions, such as transition metal‐catalyzed reactions, photoredox reactions, [5–9] and electrochemical reactions, have been developed for forming C−S bonds [10–12] . Since Migita and co‐workers reported palladium‐catalyzed cross‐coupling reactions between aryl halides and thiols, [13,14] transition‐metal‐catalyzed cross‐coupling reactions between thiols and aryl halides or their equivalents have attracted significant attention as one of the most powerful and straightforward methods of forming C−S bonds (Scheme 1a) [15–19] . Many metal salts, containing Pd, [15,19–26] Cu, [18,27–33] Ni, [8,34–39] Co, [40] Zn, [41] Au, [42,43] Ag, [44] and Rh, [45] have been used to effectively catalyze C−S cross‐coupling reactions.…”

“…[10][11][12] Since Migita and co-workers reported palladium-catalyzed cross-coupling reactions between aryl halides and thiols, [13,14] transition-metal-catalyzed crosscoupling reactions between thiols and aryl halides or their equivalents have attracted significant attention as one of the most powerful and straightforward methods of forming CÀ S bonds (Scheme 1a). [15][16][17][18][19] Many metal salts, containing Pd, [15,[19][20][21][22][23][24][25][26] Cu, [18,[27][28][29][30][31][32][33] Ni, [8,[34][35][36][37][38][39] Co, [40] Zn, [41] Au, [42,43] Ag, [44] and Rh, [45] have been used to effectively catalyze CÀ S cross-coupling reactions. Remarkable progress has been made in the field of transitionmetal-catalyzed cross-coupling reactions allowing us to access structurally diverse and polyfunctionalized sulfides.…”

Synthesis of diphenyl sulfide from iodobenzene and thiophenol using Metal-Organic Framework Cu₂(NDC)₂(DABCO) as an efficient heterogeneous catalyst

“…To overcome this drawback, other transition metals including iron, cobalt, nickel have been used as catalysts for C-S coupling reactions [6][7][8]. Unfortunately, these catalysts also have the disadvantages that are low turnover numbers, metal toxicity,…Therefore, many research groups have studied copper based catalytic systems because copper is less toxic and inexpensive [9,10]. Even though copper is found to be the most suitable catalyst for catalyzing C-S cross coupling reactions, developing an efficient catalyst containing copper system for formation C-S bonds of aryl iodides with thiols remains to be explored.…”