Asymmetric synthesis, in which chiral organocatalysts or metal complexes with chiral ligands are used, has become the most valuable methodology for the preparation of enantiomerically pure organic compounds. Among such catalysts/ligands, a growing number constitute various organosulfur compounds. This Review provides comprehensive and critical information on the plethora of sulfur-based chiral ligands and organocatalysts used in asymmetric synthesis, which have been published within the last 15 years. However, it is confined to the presentation of only those chiral catalysts/ligands that possess a stereogenic sulfur atom and includes sulfoxides, sulfinamides, N-sulfinyl ureas, sulfoximines, and some related S-chiral derivatives.

Chiral Organosulfur Ligands/Catalysts with a Stereogenic Sulfur Atom: Applications in Asymmetric Synthesis

Transition‐Metal‐Catalyzed Acyloxylation: Activation of C(sp2)–H and C(sp3)–H Bonds

A novel approach to produce chiral diaryl sulfoxides from aryl benzyl sulfoxides and aryl bromides via an enantioselective arylation of aryl sulfenate anions is reported A (JosiPhos)Pd-based catalyst successfully promotes the asymmetric arylation reaction with good functional group compatibility A wide range of enantioenriched diaryl, aryl heteroaryl, and even diheteroaryl sulfoxides were generated Many of the sulfoxides prepared herein would be difficult to prepare via classic enantioselective oxidation of sulfides, including Ph(Ph-d5)SO (90% ee, 95% yield) A DFT-based computational study suggested that chiral induction originates from two primary factors: (i) both a kinetic and a thermodynamic preference for oxidative addition that places the bromide trans to the JosiPhos-diarylphosphine moiety and (ii) Curtin–Hammett-type control over the interconversion between O- and S-bound isomers of palladium sulfenate species following rapid interconversion between re- and si-bound transmetalation products, r

Palladium-Catalyzed Enantioselective Arylation of Aryl Sulfenate Anions: A Combined Experimental and Computational Study

The chemistry of polyvalent iodine compounds has piqued the interest of researchers due to their role as important and flexible reagents in synthetic organic chemistry, resulting in a broad variety of useful organic molecules. These chemicals have potential uses in various functionalization procedures due to their non-toxic and environmentally friendly properties. As they are also strong electrophiles and potent oxidizing agents, the use of hypervalent iodine reagents in palladium-catalyzed transformations has received a lot of attention in recent years. Extensive research has been conducted on the subject of C—H bond functionalization by Pd catalysis with hypervalent iodine reagents as oxidants. Furthermore, the iodine(III) reagent is now often used as an arylating agent in Pd-catalyzed C—H arylation or Heck-type cross-coupling processes. In this article, the recent advances in palladium-catalyzed oxidative cross-coupling reactions employing hypervalent iodine reagents are reviewed in detail.

/pdf/palladium-catalyzed-organic-reactions-involving-hypervalent-1i3xb3vr.pdf

Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents

Since the original idea was explored by James in 1976, the use of chiral sulfoxides as ligands with transition metals in asymmetric catalysis has undergone a long period of development. There have been many studies into their properties, design and application in various kinds of asymmetric transformations. In this article, we document the literatures on chiral sulfoxide ligands in asymmetric catalytic reactions.

Chiral Sulfoxide Ligands in Asymmetric Catalysis.

Palladium catalyzed ortho-C–H-benzoxylation of 2-arylpyridines using iodobenzene dibenzoates

Copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones with chiral sulfoxide–phosphine ligands

Palladium catalyzed ortho-C–H-acylation of 2-arylpyridines using phenylacetylenes and styrene epoxide

The copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones was achieved with chiral sulfoxide–phosphine (SOP) ligands. This process showed good functional group tolerance and gave the 1, 4-adducts with excellent enantioselectivities (up to 96% ee).

Copper-Catalyzed Enantioselective Conjugate Addition of Diethylzinc to Acyclic Enones with Chiral Sulfoxide-Phosphine Ligands.

A palladium-catalyzed ortho-C–H-benzoxylation of 2-arylpyridines using iodobenzene dibenzoates has been developed. The reaction employed the stable and easily accessible hypervalent iodine reagents as both benzoxylate source and oxidant which made the protocol simple and facile. It showed high regioselectivity and good functional group tolerance, and gave the mono-benzoxylation products in moderate to excellent yields.

Palladium Catalyzed ortho‐C—H‐Benzoxylation of 2‐Arylpyridines Using Iodobenzene Dibenzoates.

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