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Relevant academic research and scientific papers

Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C?S/C?N Couplings

Ni-catalyzed C?S cross-coupling reactions have received less attention compared with other C-heteroatom couplings. Most reported examples comprise the thioetherification of most reactive aryl iodides with aromatic thiols. The use of C?O electrophiles in this context is almost uncharted. Here, we describe that preformed Ni(II) precatalysts of the type NiCl(allyl)(PMe2Ar’) (Ar’=terphenyl group) efficiently couple a wide range of (hetero)aryl halides, including challenging aryl chlorides, with a variety of aromatic and aliphatic thiols. Aryl and alkenyl tosylates are also well tolerated, demonstrating, for the first time, to be competent electrophilic partners in Ni-catalyzed C?S bond formation. The chemoselective functionalization of the C?I bond in the presence of a C?Cl bond allows for designing site-selective tandem C?S/C?N couplings. The formation of the two C-heteroatom bonds takes place in a single operation and represents a rare example of dual electrophile/nucleophile chemoselective process.

Ni-catalyzed C–S bond cleavage of aryl 2-pyridyl thioethers coupling with alkyl and aryl thiols

A nickel-catalyzed C–SPy bond activation reactions to produce a variety of thioethers has been developed. The reaction is promoted by a user-friendly, inexpensive, air and moisture-stable Ni precatalyst. Various aryl 2-pyridyl thioethers and a wide range of alkyl and aryl thiols substrates were tolerated in this process which afforded products in moderate to excellent yields.

Electrochemical Deoxygenative Thiolation of Preactivated Alcohols and Ketones

This work describes an electrochemically promoted nickel-catalyzed deoxygenative thiolation of alcohols and ketones under mild conditions. Excellent substrate tolerance and good chemical yields can be achieved by graphene/nickel foam electrodes in an undivided cell. Further study to gain mechanistic insight into this electrochemical cross-coupling has been carried out.

Synthesis method of alkyl sulfide compound

The invention belongs to the technical field of synthesis of organic compounds, and provides a novel method for preparing an alkyl sulfide compound. According to the method, direct synthesis preparation of the thioether compound is realized by utilizing direct coupling of an organic sulfinic acid compound and alkane under acid and illumination conditions. According to the present invention, the alkane C-H bond direct thioetherification method is adopted, the reaction functional group does not need to be configured in advance, the thioether compound synthesis reaction steps are substantially shortened, the raw materials are cheap and easily available, the conditions are mild and green, the operation is simple, convenient and safe, and the good economic prospect is provided.

Visible-Light-Mediated Alkylation of Thiophenols via Electron Donor-Acceptor Complexes Formed between Two Reactants

A metal-free, photocatalyst-free, photochemical system was developed for the direct alkylation of thiophenols via electron donor-acceptor (EDA) complexes (KEDA = 145 M-1) between two reactants, N-hydroxyphthalimide esters as acceptors and thiophenol anions as donors, in the presence of a tertiary amine. The EDA complexes in the reaction system have a broad range of visible-light absorption (400-650 nm) and can trigger the reaction effectively under sunlight.

Thioether ligand-enabled cationic palladium (II)-catalyzed electrophilic C-H arylation of α,β-unsaturated oxime ethers

The use of the cationic palladium(II) catalyst realized electrophilic C-H arylation of α,β-unsaturated O-SEM oximes with arylboronic acids. This Pd-catalyzed electrophilic C-H arylation is facilitated by employing alkyl aryl thioether ligands, and optimization of the ligand structure greatly improves the yield. The resulting α,β-unsaturated oximes would provide access to multisubstituted heterocyclic compounds.

Deprotonated Salicylaldehyde as Visible Light Photocatalyst

Salicylaldehyde is established as an efficient visible light photocatalyst for the first time. Compared to other simple aldehyde analogies, salicylaldehyde has a unique deprotonative red-shift from 324 to 417 nm and gives rise to the remarkable increase of fluorescence quantum from 0.0368 to 0.4632, thus enabling salicylaldehyde as a visible light (>400 nm) photocatalyst. The experimental investigations suggest that the reactive radical species are generated by sensitization of the substrates by the deprotonated salicylaldehyde through an energy-transfer pathway. Consequently, the C-C cleaving alkylation reactions of N-hydroxyphthalimide esters proceed smoothly in the presence of as low as 1 mol % of salicylaldehyde under the visible-light irradiation, affording desired alkylation products with up to 99% yields. Application in visible-light induced aerobic oxidation of N-alkylpyridinium salts is also reported.

Nickel-Catalyzed Inter- and Intramolecular Aryl Thioether Metathesis by Reversible Arylation

A nickel-catalyzed aryl thioether metathesis has been developed to access high-value thioethers. 1,2-Bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional-group-tolerant reaction. Furthermore, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis that does not involve alkene bonds. In-depth organometallic studies support a reversible Ni0/NiII pathway to product formation. Overall, this work not only provides a more sustainable alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information that are highly relevant to the further development and application of unusual single-bond metathesis reactions.

Forging C-S Bonds through Nickel-Catalyzed Aryl Anhydrides with Thiophenols: Decarbonylation or Decarbonylation Accompanied by Decarboxylation

A nickel-catalyzed decarbonylation or decarbonylation accompanied by decarboxylation cross-coupling reaction of aryl anhydrides with thiophenols as coupling partners was disclosed. This method is promoted by a commercially available, moisture-stable, and inexpensive nickel(II) precatalyst. The process can tolerate a variety of functional groups using ubiquitous aryl anhydrides as cross-coupling precursors to produce thioethers in moderate to excellent yields.

Copper-Catalyzed Electrophilic Thiolation of Organozinc Halides by Using N-Thiophthalimides Leading to Polyfunctional Thioethers

(Hetero)aryl, benzylic, and alkyl zinc halides were thiolated with N-thiophthalimides at 25 °C within 1 h in the presence of 5–10 % Cu(OAc)2?H2O to furnish the corresponding polyfunctionalized thioethers in good yields. This electrop