Copper‐Catalyzed Double S‐Arylation of Potassium Thioacetate with Dibenziodolium Triflates: Facile Synthesis of Unsymmetrical Dibenzothiophenes

Shimizu, Masaki; Ogawa, Mai; Tamagawa, Tomokazu; Shigitani, Ryosuke; Nakatani, Masaki; Nakano, Yoshiki

doi:10.1002/ejoc.201600357

Cited by 47 publications

(20 citation statements)

References 59 publications

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“…In 2016, Shimizu et al. developed a copper‐catalyzed double S‐arylation of potassium thioacetate (KSAc) with cyclic diaryliodonium salts for the construction of dibenzothiophenes (Scheme ) . The unsymmetrical cyclic diaryliodonium salts with electron‐donating or electron‐withdrawing groups led to the corresponding dibenzothiophenes products in good to excellent yields.…”

Section: Cyclic Diaryliodonium Saltsmentioning

confidence: 99%

Atom‐Economical Applications of Diaryliodonium Salts

Wang

Chen

Jiang

2018

Chemistry An Asian Journal

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Diaryliodonium salt, as a stable and easily prepared reagent, has become one of the most efficient arylation reagents in organic synthesis. In traditional methods, this reagent is generally applied as a single arylation source and the regenerated aryl iodide is a waste of resources. In the past five years, transition-metal-catalyzed utilization of both aryl groups in diaryliodonium salts has been well demonstrated. The purpose of the present review is to focus on various atom-economical applications of diaryliodonium salt methodologies that have been reported recently for the synthesis of functionalized molecules. The presentation is organized according to the structures of the diaryliodonium salts and the reaction components.

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Section: Cyclic Diaryliodonium Saltsmentioning

confidence: 99%

Atom‐Economical Applications of Diaryliodonium Salts

Wang

Chen

Jiang

2018

Chemistry An Asian Journal

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“…Compounds containing para-disubstituted benzene fragments were found, and these displayed a range of conformations at the C-S bond (Figure 11). Phthalocyanin JUBPON, 37 symmetrically substituted at the 1,4,8,11,15,18,22,25 (all ortho-) positions with hexylsulfanyl groups, adopted a nearly completely planar structure. The substituents were fully extended with almost all lying in the plane of the core and turned away from the bridging (6,13,20,27) nitrogen atoms.…”

Section: Packingmentioning

confidence: 99%

Effect of Alkyl Chain Length and Linker Atom on the Crystal Packing in 6,12-Dialkoxy- and 6,12-Dialkylsulfanyl-Benzo[1,2-b:4,5-b′]bis[b]benzothiophenes

Riaz

Edgar

Elsegood

et al. 2019

Crystal Growth & Design

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The effect of varying the chain length on the solid state conformation and packing of 6,12-dialkoxy- and 6,12-dialkylsulfanyl-benzo[1,2-b:4,5-b′]bis[b]benzothiophenes has been studied. The compounds were prepared by SNAr reaction of 6,12-difluorbenzo[1,2-b:4,5-b′]bis[b]benzothiophene with alkoxides or alkanethiolates derived from C7–C10 alcohols and alkanethiols. Single crystal X-ray diffraction analysis revealed that all but two compounds crystallize in the triclinic space group P . Two compounds were obtained as monoclinic crystals with space group P21/c. The alkoxy substituted compounds adopted a molecular conformation with a step from the core and a gauche conformation about the C1′–C2′ bond placing the alkyl chains close to parallel with the pentacyclic arene ring system, whereas in the alkylsufanyl derivatives, the alkyl chains were arranged strongly deviated from the plane of the ring, with the sulfur atom antiperiplanar to C3′ of the alkyl chain. NMR measurement of T1 relaxation in CDCl3 showed both the alkoxy and alkylsulfanyl substituents to be freely rotating at ambient temperature in solution, indicating the orientation of the chains in the solid state was due to packing interactions during crystallization.

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“…The group of Shimizu has reported the formation of dibenzothiophenes 66 following the reaction of cyclic diaryl-λ 3 -iodanes with potassium thioacetate as the sulfur donor, and CuCl 2 as the catalyst ( Scheme 29 ) [ 69 ]. The reaction can be performed either in THF or DMSO, affording both symmetrical and non-symmetrical products in good to excellent yields.…”

Section: Reviewmentioning

confidence: 99%

Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

Grelier¹,

Darses²,

Dauban³

2018

Beilstein J. Org. Chem.

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Most of the polyvalent organoiodine compounds derive from iodoarenes, which are released in stoichiometric amounts in any reaction mediated by λ3- or λ5-iodanes. In parallel to the development of solid-supported reagents or reactions catalytic in iodine, a third strategy has emerged to address this issue in terms of sustainability. The atom-economy of transformations involving stoichiometric amounts of λ3- or λ5-iodanes, thus, has been improved by designing tandem reactions that allows for incorporating the aryl motif into the products through a subsequent one-pot nucleophilic addition or catalytic coupling reaction. This review summarizes the main achievements reported in this area.

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Copper‐Catalyzed Double S‐Arylation of Potassium Thioacetate with Dibenziodolium Triflates: Facile Synthesis of Unsymmetrical Dibenzothiophenes

Cited by 47 publications

References 59 publications

Atom‐Economical Applications of Diaryliodonium Salts

Atom‐Economical Applications of Diaryliodonium Salts

Effect of Alkyl Chain Length and Linker Atom on the Crystal Packing in 6,12-Dialkoxy- and 6,12-Dialkylsulfanyl-Benzo[1,2-b:4,5-b′]bis[b]benzothiophenes

Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

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