Dual Selectivity: Electrophile and Nucleophile Selective Cross-Coupling Reactions on a Single Aromatic Substrate

Heinrich, A.; Thiedemann, Birk; Gates, Paul J.; Staubitz, Anne

doi:10.1021/ol401923j

Cited by 36 publications

(31 citation statements)

References 56 publications

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“…Reagent grade solvents were distilled prior to use. Compounds 1 [21] and 2, [22] and 6c [33] were prepared according to the reported procedures. 1 H, 13 C, 11 BNMR, and 2D NMR spectra were recorded on aB ruker Avance4 00 spectrometer or aB ruker DMX 600 spectrometer 1 H, and 13 CNMR spectra were calibrated to the residual solvent signals.…”

Section: Methodsmentioning

confidence: 99%

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n‐Channel Organic Semiconductors Derived from Air‐Stable Four‐Coordinate Boron Complexes of Substituted Thienylthiazoles

Hecht

Kade

Schmidt

et al. 2017

Chemistry A European J

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Three acceptor-π-bridge-acceptor (A-π-A) molecules derived from 2-(3-boryl-2-thienyl)thiazole have been synthesized and thoroughly characterized. Incorporation of a B-N unit into thienylthiazole and attachment of suitable acceptor moieties allowed to obtain ambient-stable A-π-A molecules with low-lying LUMO levels. Their potential for applications in organic electronics was tested in vacuum-deposited organic thin film transistors (OTFT). The OTFT device based on boryl-thienylthiazole and 1,1-dicyanomethylene-3-indanone (DCIND) acceptor moieties showed an electron mobility of ≈1.4×10 cm V s in air, which is the highest electron mobility reported to date for organoboron small molecules. Conversely, the device employing the malononitrile (MAL) derivative as an active layer did not show any charge transport behavior. As suggested by single crystal X-ray analysis of indandione (IND) and MAL derivatives, the enhanced mobility of IND (and DCIND) in comparison to the MAL molecule can be attributed to the effective two-dimensional π-stacking in the solid state imparted by the acceptor moieties with an extended π-surface.

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Section: Methodsmentioning

confidence: 99%

“…3-Bromo-2-iodothiophene (1) [21] and 2-(tributylstannyl)thiazole (2) [22] were prepared according to the reported procedures. 3-Bromo-2-iodothiophene (1) [21] and 2-(tributylstannyl)thiazole (2) [22] were prepared according to the reported procedures.…”

Section: Design Considerations and Synthesismentioning

confidence: 99%

n‐Channel Organic Semiconductors Derived from Air‐Stable Four‐Coordinate Boron Complexes of Substituted Thienylthiazoles

Hecht

Kade

Schmidt

et al. 2017

Chemistry A European J

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“…An important issue to be addressed in the mono-cross-coupling of dihaloarenes is the selectivity between the two halo groups. In general, the intrinsic difference in the reactivity of the halo groups (i.e., I > Br > Cl > F) can be utilized to realize chemoselective cross-coupling at the desired position [4][5][6][7]. Interesting examples of chemoselectivity controlled by the catalysts used have been also reported [8][9][10].…”

Section: Open Accessmentioning

confidence: 99%

Catalyst-Controlled Site-Selectivity Switching in Pd-Catalyzed Cross-Coupling of Dihaloarenes

Manabe

Yamaguchi

2014

Catalysts

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Pd-catalyzed, site-selective mono-cross-coupling of substrates with two identical halo groups is a useful method for synthesizing substituted monohalogenated arenes. Such arenes constitute an important class of compounds, which are commonly identified as drug components and synthetic intermediates. Traditionally, these site-selective reactions have been realized in a "substrate-controlled" manner, which is based on the steric and electronic differences between the two carbon-halogen bonds of the substrate. Recently, an alternative strategy, "catalyst-controlled" site-selective cross-coupling, has emerged. In this strategy, the preferred reaction site of a dihaloarene can be switched, merely by changing the catalyst used. This type of selective reaction further expands the utility of Pd-catalyzed cross-coupling. In this review, we summarize the reported examples of catalyst-controlled site-selectivity switching in Pd-catalyzed cross-coupling of dihaloarenes.

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“…[53] To overcome this issue, ah ighly nucleophile selective cross-coupling reaction had to be performed that would not only leavethe stannole intact, but would also be highly effective because the length of ap olymer using step growth polycondensation methods depends on the conversion of the polymerization reaction (Carothers equation). [48,60] At hiophene flankeds tannole monomer with peripheral iodide functional groups 40 as an electrophilic component and ab is(ditrimethyltin) thiophene 84 as the nucleophilic monomer allowed the successful preparation of the polymer 85 using aS tille cross-coupling reaction( Scheme 27). [49] The dark purple polymer had ar elatively high molecularw eighto fM W = 17.0 kDa (gel permeation chromatography standard calibration against polystyrene), whichd emonstrates the very high selectivity of the reactione ven under harsh conditions, that is, refluxingt oluene.F or the optoelectronic properties of this polymer,see below.…”

Section: Stannoles In Polymersmentioning

confidence: 99%

Syntheses and Properties of Tin‐Containing Conjugated Heterocycles

Urrego-Riveros

Medina

Hoffmann

et al. 2018

Chemistry A European J

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Heterocycles that contain tin atoms can be aromatic in a similar sense to well-known aromatic compounds such as benzene or thiophene, but such examples are rare. However, due to the low-lying σ*-orbitals of the tin-substituent bond in stannoles, they are capable of σ*-π* conjugation in a way that is exclusive to heavier element containing heterocycles. This makes stannoles very interesting alternatives for purely organic heterocycles in material applications, in which optoelectronic properties are of interest. This Concept article will highlight the synthesis, reactivity and physical properties of stannoles and related fluorenostannoles. At first, a brief introduction to different types of tin-containing heterocycles is presented, followed by a discussion on different approaches to prepare stannoles, their reactivity and their physical properties. In addition, the first stannole-containing polymer will be reviewed.

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Dual Selectivity: Electrophile and Nucleophile Selective Cross-Coupling Reactions on a Single Aromatic Substrate

Cited by 36 publications

References 56 publications

n‐Channel Organic Semiconductors Derived from Air‐Stable Four‐Coordinate Boron Complexes of Substituted Thienylthiazoles

n‐Channel Organic Semiconductors Derived from Air‐Stable Four‐Coordinate Boron Complexes of Substituted Thienylthiazoles

Catalyst-Controlled Site-Selectivity Switching in Pd-Catalyzed Cross-Coupling of Dihaloarenes

Syntheses and Properties of Tin‐Containing Conjugated Heterocycles

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