Recent developments in palladium-catalyzed C–S bond formation

Abstract

This review summarized the recent developments in palladium-catalyzed C–S bond formation involving sulfenylation and sulfonylation reactions.

Palladium‐CatalyzedSequential Cyclization/Functionalization of Oxime Ethers with Unactivated Vinyl Ethers for Tunable Assembly of Structurally Diverse Isoxazoles

“…transition‐metal‐catalyzed coupling reaction using the unactivated vinyl ethers as the alkenyl sources is highly desirable. With our continuing interests in palladium‐catalyzed tandem reactions of alkynes with alkenes, [ 20 ] we herein described a palladium‐catalyzed sequential cyclization/functionalization of O ‐methyl oximes with unactivated vinyl ethers for tunable assembly of structurally diverse isoxazoles (Scheme 1c).…”

Thiofunctionalization of Electron‐Rich Heteroarenes through Magnesiation and Trapping with Octasulfur

“…Indeed, the high potential of pharmacomodulations offered by the sulfur atom, considering its further attachment to carbon or heteroatoms and the possibilities offered by its oxidized forms, made this particular motif a classic of the medicinal chemist's palette [3] . Efficient methodologies such as S N Ar or cross‐couplings with thiols and metal‐halogen exchanges followed by trapping with disulfides have been developed to functionalize electron‐poor heteroarenes with sulfur atom from the corresponding heteroarylhalides [4,5] . In the case of electron‐rich heteroarenes, these synthetic methodologies are not always applicable, despite the description of numerous active substances in which the sulfur atom is attached to a nitrogen contained in the heterocycle (Figure 1, N−C−S sequence).…”

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.…”