Tandem photocyclization-intramolecular addition reactions of aryl vinyl sulfides. Observation of a novel [2 + 2] cycloaddition-allylic sulfide rearrangement

Dittami, James P.; Nie, Xiao Yi; Nie, Huixiang; Ramanathan, H.; Buntel, Christopher J.; Rigatti, S.; Bordner, Jon; Decosta, D. L.; Williard, Paul G.

doi:10.1021/jo00030a022

Cited by 30 publications

(12 citation statements)

References 4 publications

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“…They can also be used in Michael, Peterson, or Diels-Alder transformations as well being easily reductively cleaved. [395][396][397][398][399][400][401] Vinylsulfides were isolated in the biologically active compounds e.g., Griseoviridin from Streptomyces graminofaciens or benzylthiocrellidone from Crella spinulata. [402][403][404] Nucleophilic addition of thiolate anions to CRC bonds in alkynes and diynes occurs mainly according to a trans-addition reaction with the generation of (Z)-vinylic isomers.…”

Section: Hydrophosphination Of Conjugated and Non-conjugated Diynesmentioning

confidence: 99%

Hydroelementation of diynes

et al. 2022

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Section: Hydrophosphination Of Conjugated and Non-conjugated Diynesmentioning

confidence: 99%

Hydroelementation of diynes

et al. 2022

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“…Workup of the reaction resulted in a yellow oil (0.3062 g, 87%). 1 Phenyl(4-((3-(styrylthio)propyl)thio)phenyl)methanone (8). The title compound was prepared using the general procedure with 4-bromobenzophenone (0.2609 g, 1.0 mmol).…”

Section: Scheme 4 Control Experimentsmentioning

confidence: 99%

Synthesis of Disubstituted Dithioethers: tert-Butoxide Promoted Elimination/Ring Opening of 1,3-Dithianes Followed by Palladium-Catalyzed C–S Bond Formation

Abidi

Schmink

2015

J. Org. Chem.

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We report the tandem base-promoted elimination/ring-opening of 2-benzyl-1,3-dithianes with subsequent cross coupling of the pendent thiol with a range of aryl bromides. A simple Pd(OAc)2/Xantphos catalyst system affects this new reaction and is compatible with a wide range of functional groups, including heteroaromatic coupling partners. The transformation proceeds in good to excellent yields (69-99%) and exhibits strong stereoselectivity, forming the E-alkene as the major diastereomer. This new methodology provides access to nonsymmetric propylene styryl/aryl dithioethers, a previously undisclosed motif.

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“…When the naphthylthioether derivative 109 was irradiated, first a pericylic reaction occurred, leading in a high yield to the naphtothiophene derivative 110 (Scheme 17). 86 Such pericyclic reactions with aromatic compounds have frequently been applied to organic synthesis. 24,29,87 When the reaction is carried out at a low temperature, the transformation is stopped at the stage of 110.…”

Section: Photocycloadditions With Condensed Aromatic Compoundsmentioning

confidence: 99%

Photochemical reactions of aromatic compounds and the concept of the photon as a traceless reagent

Hoffmann

2012

Photochem Photobiol Sci

119

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Electronic excitation significantly changes the reactivity of chemical compounds. Compared to ground state reactions, photochemical reactions considerably enlarge the application spectrum of a particular functional group in organic synthesis. Multistep syntheses may be simplified and perspectives for target oriented synthesis (TOS) and diversity oriented synthesis (DOS) are developed. New compound families become available or may be obtained more easily. In contrast to common chemical reagents, photons don't generate side products resulting from the transformation of a chemical reagent. Therefore, they are considered as a traceless reagent. Consequently, photochemical reactions play a central role in the methodology of sustainable chemistry. This aspect has been recognized since the beginning of the 20th century. As with many other photochemical transformations, photochemical reactions of aromatic, benzene-like compounds illustrate well the advantages in this context. Photochemical cycloadditions of aromatic compounds have been investigated for a long time. Currently, they are applied in various fields of organic synthesis. They are also studied in supramolecular structures. The phenomena of reactivity and stereoselectivity are investigated. During recent years, photochemical electron transfer mediated reactions are particularly focused. Such transformations have likewise been performed with aromatic compounds. Reactivity and selectivity as well as application to organic synthesis are studied.

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Tandem photocyclization-intramolecular addition reactions of aryl vinyl sulfides. Observation of a novel [2 + 2] cycloaddition-allylic sulfide rearrangement

Cited by 30 publications

References 4 publications

Hydroelementation of diynes

Hydroelementation of diynes

Synthesis of Disubstituted Dithioethers: tert-Butoxide Promoted Elimination/Ring Opening of 1,3-Dithianes Followed by Palladium-Catalyzed C–S Bond Formation

Photochemical reactions of aromatic compounds and the concept of the photon as a traceless reagent

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