4.5 Review

Recent Advances in Thianthrenation/Phenoxathiination Enabled Site-Selective Functionalization of Arenes

Related references

Note: Only part of the references are listed.
Article Multidisciplinary Sciences

Tritiation of aryl thianthrenium salts with a molecular palladium catalyst

Da Zhao et al.

Summary: Tritium labelling is a critical tool for pharmacokinetic and pharmacodynamic studies, and tritium gas is preferred for labelling due to its high isotopic purity. While heterogeneous catalysts like palladium supported on carbon are commonly used for tritiation reactions, their reaction mechanism can result in the reduction of other functional groups present in pharmaceuticals.

NATURE (2021)

Article Chemistry, Organic

Construction of α-Amino Azines via Thianthrenation-Enabled Photocatalyzed Hydroarylation of Azine-Substituted Enamides with Arenes

Yu-Lan Zhang et al.

Summary: The study presents a practical method for accessing alpha-amino azines through a photocatalyzed hydroarylation reaction. This method demonstrates a broad substrate scope, good functional group tolerance, mild reaction conditions, and is suitable for the late-stage installation of alpha-amino azines in complex structures.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Diverse C-P Cross-Couplings of Arylsulfonium Salts with Diarylphosphines via Selective C-S Bond Cleavage

Yun Ye et al.

Summary: The study demonstrates that the reaction of arylthianthrenium salts with diarylphosphines can undergo phosphination via the cleavage of either an endocyclic or exocyclic C-S bond, with significantly higher speed in the presence of a palladacycle catalyst.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

Late-Stage Heteroarylation of Hetero(aryl)sulfonium Salts Activated by α-Amino Alkyl Radicals

Eva Maria Alvarez et al.

Summary: This study presents a novel method for late-stage heteroarylation of aryl sulfonium salts using alpha-amino alkyl radicals, which differs mechanistically from previously reported halogen-atom transfer (XAT). The new activation mode of aryl sulfonium salts can be carried out in the absence of light and photoredox catalysts, and is applicable to a wide range of heterocycles, showing potential for useful cross-coupling transformations.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Pd/Cu-Catalyzed C-H/C-H Cross Coupling of (Hetero)Arenes with Azoles through Arylsulfonium Intermediates

Ze-Yu Tian et al.

Summary: A selective formal C-H/C-H cross-coupling of azoles and (hetero)arenes was established using arylsulfonium intermediates under transition-metal catalysis, providing a variety of 2-(hetero)aryl azoles in good to excellent yields. The advantages of this reaction include mild reaction conditions, good functional group tolerance, a wide substrate scope, high regio- and chemoselectivity, one-pot procedures, and late-stage functionalization of complex molecules without the use of oxidants, offering a promising strategy for transition-metal-catalyzed C-H arylation of azoles.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

Site-Selective C-H alkylation of Complex Arenes by a Two-Step Aryl Thianthrenation-Reductive Alkylation Sequence

Beatrice Lansbergen et al.

Summary: In this study, an undirected para-selective two-step C-H alkylation method for complex arenes useful for late-stage functionalization is presented. By combining site-selective C-H thianthrenation with palladium-catalyzed reductive electrophile cross-coupling, a diverse range of synthetically useful alkylated arenes can be accessed with high selectivity and practicality. The robustness of this transformation is further demonstrated by thianthrenium-based reductive coupling of two complex fragments.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

High Site Selectivity in Electrophilic Aromatic Substitutions: Mechanism of C-H Thianthrenation

Fabio Julia et al.

Summary: The use of thianthrene as a linchpin in aromatic C-H functionalization reactions has been studied experimentally and computationally, revealing the mechanism and unique site selectivity of the reaction.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

Yue Zhao et al.

Summary: The construction of (hetero)biaryls through a photoinduced and catalyst-free C-H/C-H cross-coupling provides a simple and efficient synthetic approach by selectively forming aryl thianthrenium salts. Using UV-light to disrupt the C-S bond allows for the formation of thianthrene radical cations and aryl radicals.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

Regio- and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles

Junting Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Photoredox catalysis with aryl sulfonium salts enables site-selective late-stage fluorination

Jiakun Li et al.

NATURE CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Pd-Catalyzed Site-SelectiveBorylation of Simple Arenes via Thianthrenation

Xiao-Yue Chen et al.

CHINESE JOURNAL OF CHEMISTRY (2020)

Article Chemistry, Organic

Site-Selective C-H Functionalization-Sulfination Sequence to Access Aryl Sulfonamides

Eva Maria Alvarez et al.

ORGANIC LETTERS (2020)

Article Chemistry, Organic

Germylation of Arenes via Pd(I) Dimer Enabled Sulfonium Salt Functionalization

Aymane Selmani et al.

ORGANIC LETTERS (2020)

Article Chemistry, Organic

Cine-Substitutions at Five-Membered Hetarenes Enabled by Sulfonium Salts

Florian Berger et al.

ORGANIC LETTERS (2020)

Article Chemistry, Organic

Site-Selective Silylation of Arenes Mediated by Thianthrene S-Oxide

Yichen Wu et al.

ORGANIC LETTERS (2020)

Article Chemistry, Organic

Thianthrenation-Enabled α-Arylation of Carbonyl Compounds with Arenes

Xiao-Xue Nie et al.

ORGANIC LETTERS (2020)

Article Multidisciplinary Sciences

Site-selective and versatile aromatic C-H functionalization by thianthrenation

Florian Berger et al.

NATURE (2019)

Article Chemistry, Multidisciplinary

C-N Cross-Couplings for Site-Selective Late-Stage Diversification via Aryl Sulfonium Salts

Pascal S. Engl et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Aryl Sulfonium Salts for Site-Selective Late-Stage Trifluoromethylation

Fei Ye et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Site-selective C-H Oxygenation via Aryl Sulfonium Salts

Ruocheng Sang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)