A General Palladium-Catalyzed Coupling of Aryl Bromides/Triflates and Thiols

Abstract

We have developed an efficient palladium-catalyzed carbon-sulfur bond formation reaction of aryl bromides, triflates, and activated aryl chloride. Using this protocol, we have shown tolerance to a wide variety of aryl thiols and alkyl thiols that can also be used as sulfide equivalents. [reaction: see text]

Highly Strained Tertiary sp3 Scaffolds: Synthesis of Functionalized Cubanes and Exploration of Their Reactivity under Pd(II) Catalysis

“…24 As a conclusion to the work on lithiated cubanes an alternative and more general method for the introduction of sulfur onto the cubane core in a milder fashion was investigated. Reaction of 4 with a sulfenyl chloride (derived from an odorless thiol which undergoes ready base deprotection to the free thiol [33][34][35] ) was found to give a low yield of the sulfur appended cubane 18 (Table 2, Entry 14). Difficulties involving the dimerization of the sulfenyl chloride species lowered the reaction yield.…”

Transition metal- and solvent-free synthesis of unsymmetrical diaryl sulfides and selenides under ball-milling

“…6 Hence there has been an obvious interest towards the development of synthetic methodologies for the synthesis of these compounds. The majority of the reported protocols involved transition metals like Pd, [7][8] Cu, [9][10][11][12] Ni, [13][14][15] and Fe [16][17][18] in the reaction of aryl halides or aryl boronic acids to form chalcogenides. But few transition metal-free procedures were also reported for the reaction of aryl diazonium salts and lithium, sodium and potassium salt of arene thiolate / selenolate/ tellurolate.…”

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

“…5 Many other Pd based catalytic systems have also been developed, which are based on bidentate phosphines or diverse organophosphane derivatives. [6][7][8][9] But these systems have limitations since they require the preparation and use of PR 3 ligands which are not eco-friendly. Catalytic systems based on other transition metals such as nickel [10][11][12][13] , cobalt 14 and iron 15 have also been studied.…”