Synthesis of α‐oxo‐sulfines in the indole series

Bergman, Jan; Romero, Iván

doi:10.1002/jhet.453

Cited by 16 publications

(7 citation statements)

References 29 publications

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“…Unusually, activation of the methylene group was not required, due to the aromaticity of the system. [53] Scheme 18. Reaction of oxindole with thionyl chloride.…”

Section: Sulfenylation Of Activated Methylene Compoundsmentioning

confidence: 99%

Generation, Reactivity and Uses of Sulfines in Organic Synthesis

et al. 2016

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This review focuses on the synthesis and reactivity of thioketone S‐oxides (sulfines). Sulfines have been long established as being reactive intermediates of high interest and with potential for wide application in organic synthesis. The review will cover many aspects of sulfines: the first section looks at the different routes to the synthesis of these compounds with a detailed look at more recently developed routes; the second section details the scope of reactivity of these types of compounds and how they are useful in synthetic organic chemistry with a particular look at cycloaddition and nucleophilic addition reactions.

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“…Unusually, activation of the methylene group was not required, due to the aromaticity of the system. [53] Scheme 18. Reaction of oxindole with thionyl chloride.…”

Section: Sulfenylation Of Activated Methylene Compoundsmentioning

confidence: 99%

Generation, Reactivity and Uses of Sulfines in Organic Synthesis

et al. 2016

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“…34 It was shown that the first stage of the reaction results in the formation of the corresponding α-oxosulfine (12) which further produces isoindigo in almost quantitative yield (Scheme 6). But this approach was limited and can't be applied on SOCl 2 sensitive groups such as hydroxyl, acid and amine scaffolds.…”

Section: Methodsmentioning

confidence: 99%

Advances in the synthesis and application of isoindigo derivatives

Богданов¹,

Musin²,

Миронов³

2015

Arkivoc

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“…[27,48,49] For the tactic using oxindole as precursor, in the presence of SOCl 2 , oxindole is converted to a sulfoxide intermediate, followed by dimerization in acetonitrile to produce isoindigo (Figure 1e). [50] As shown in Figure 1f, some center-inserted isoindigo derivatives can be synthesized by the Knoevenagel condensation with oxindole as a precursor. [51][52][53] Wan's group synthesized a isoindigo derivative using an oxindole-based precursor.…”

Section: Synthetic Tactics Of Isoindigo and Its Derivativesmentioning

confidence: 99%

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

Wei

Zhang

2021

Adv Funct Materials

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(1 of 33)benzothiadiazole (BT), [8,9] naphthalene diimide (NDI), [10,11] and isoindigo. [12][13][14] Isoindigo is an isomer of the wellknown industrial dye indigo and can be directly isolated from nature. [15,16] The structural difference between isoindigo and indigo is the relative positions of the nitrogen atom and the carbonyl group. In the indigo molecule, the nitrogen atoms are not connected to the carbonyl groups. Moreover, the nitrogen atoms in isoindigo molecule are connected with carbonyl groups. In 2012, indigo was reported as the active layer material of organic fieldeffect transistors (OFETs), which exhibited well-balanced ambipolar transport. [17] However, the H-bonded indigo showed extremely low solubility. For achieving good solution processibility, solubilizing side chains are introduced on the nitrogen atoms, which on the other hand break the intramolecular hydrogen bond, thereby reducing the molecular conjugation and limiting the electronics applications. [18] By contrast, the side chains on isoindigo do not break the hydrogen bond, and thus isoindigo is considered as a superior building block for organic electronic materials. [18,19] Since isoindigo was first used in organic electronics in 2010, [20] isoindigo-derived conjugated polymers have attracted considerable attention and have been developed rapidly due to the strong electron deficiency and high molecular planarity of isoindigo unit. [12,21] Moreover, compared with DPP, BT or NDI, isoindigo has a π-framework that can be readily modified. The structural feature of isoindigo endows itself many modification sites, including the side chains attached to the lactam nitrogen atoms, the center double bond, and the phenyl rings. More than twenty isoindigo derivatives have been reported. [22][23][24][25][26][27][28] Based on isoindigo and its derivatives, various isoindigo-derived conjugated polymers have been synthesized and many of them showed excellent performance. For example, using isoindigo-derived conjugated polymers, the hole and electron mobilities of p-and n-type OFETs have reached 14.4 and 14.9 cm 2 V −1 s −1 , respectively, and some ambipolar OFETs exhibited high hole/electron mobilities of up to 5.97/7.07 cm 2 V −1 s −1 . [29][30][31] The power conversion efficiencies (PCEs) of fullerene-containing organic photovoltaics (OPVs) and all-polymer solar cells (all-PSCs) based on isoindigo-derived polymers have exceeded 10% and 7%, respectively. [32,33] Furthermore, various structural modification

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Synthesis of α‐oxo‐sulfines in the indole series

Cited by 16 publications

References 29 publications

Generation, Reactivity and Uses of Sulfines in Organic Synthesis

Generation, Reactivity and Uses of Sulfines in Organic Synthesis

Advances in the synthesis and application of isoindigo derivatives

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

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