Triphyrin catalyzed direct C–H arylation of benzene with aryl halides

Ng, Yeuk Sze; Chan, Chung Sum; Chan, Kin Shing

doi:10.1016/j.tetlet.2014.09.043

Cited by 19 publications

(9 citation statements)

References 31 publications

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“…Later, different research groups have reported the synthesis of biaryl compounds starting from unactivated arenes by direct C–H activation using NaO t Bu or KO t Bu in the presence of different organic additives such as ligands and super electron donors (SED) (Figure ). − This success in C–H aromatic substitution was followed by C–H functionalization of styrenes with ArX through a similar base-promoted mechanism. − …”

Section: Introductionmentioning

confidence: 99%

Initiation in Photoredox C–H Functionalization Reactions. Is Dimsyl Anion a Key Ingredient?

et al. 2017

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Previous studies have reported the arylation of unactivated arenes with ArX, base (KOBu or NaOBu), and an organic additive at high temperatures. Recently, we showed that this reaction proceeds in the absence of additives at rt but employs UV-vis light. However, details of mechanisms that can use a photoinduced base-promoted homolytic aromatic substitution reaction (photo-BHAS) have remained elusive until now. This work examines different mechanistic routes of the essential electron-transfer step (ET) of this reaction in order to identify a possible path for the formation of 1-adamantyl radicals from 1-haloadamantanes (initiation step). On the basis of photochemical and photophysical experiments and computational studies, we propose an unprecedented initiation step that could also be applied to other ET reactions performed in DMSO. For the first time, it is reported that dimsyl anion, formed from a strong base and DMSO (solvent), is responsible for inducing the initiation by a photo-BHAS process on alkyl halides.

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Section: Introductionmentioning

confidence: 99%

Initiation in Photoredox C–H Functionalization Reactions. Is Dimsyl Anion a Key Ingredient?

et al. 2017

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“…Srinivasan and co-workers also reported the meso-aryl -free [14]triphyrins(2.1.1) 7 and 10a-d (Scheme 2). 8 [14]Triphyrins(2.1.1) can be used as catalysts for C-H arylations 9 or reductions of dioxygen compounds. 10 The photophysical properties of [14]triphyrins(2.1.1) have been investigated by time-resolved fluorescence techniques to study their excited-state dynamics.…”

Section: Introductionmentioning

confidence: 99%

Porphyrinoids with Vinylene Bridges

Kuzuhara

Yamada

2020

Synlett

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Porphyrinoids containing vinylene bridges, such as triphyrin(2.1.1), porphycene, porphyrin(2.1.2.1), and hexaphyrin(2.1.2.1.2.1), are a relatively new family of porphyrinoids. Vinylene bridges give porphyrinoids a lower symmetry and a flexibility of the framework and they permit cis/trans-isomerization reactions; these factors confer unique properties to these substances, such as coordination to metal ions and aromaticity switching. In this account, the synthesis, crystal structures, and properties of new porphyrinoids containing vinylene bridges are summarized.1 Introduction2 Triphyrin(2.1.1)3 Porphycene4 Porphyrin(2.1.2.1)5 Hexaphyrin(2.1.2.1.2.1)6 Conclusion

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“…Triphyrins (Scheme 1) constitute ar elatively new porphyrinoid family, [1,2] including macrocycles dispersed in size from the smallest classical triphyrins(1.1.1) [3,4] in their basic tripyrrolic form known only as boron(III) complexes, through versatile ligands,t riphyrins(2.1.1), [5][6][7][8][9][10] then modestly represented triphyrins(3.1.1) [11][12][13][14] to triphyrins(4.1.1), [15][16][17][18][19] and finally to av ery flexible macrocycle,t riphyrin(6.1.1). [20][21][22][23][24] The above triphyrin(n.1.1) series does not include the very first heterotriphyrins(2.2.2) reported by Badgere tal., [25,26] named [ 18]annulene sulfides/ oxides.…”

Section: Introductionmentioning

confidence: 99%

Shaping a Porphyrinoid Frame by Heteroatoms Extrusion: Formation of an Expanded [22]Triphyrin(6.6.0)

Pacholska‐Dudziak

Latos‐Grażyński

Białońska

2019

Chemistry A European J

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An aromatic expanded triphyrin, [22]triphyrin(6.6.0) 2, containing a pyrrole unit, a bipyrrole moiety, and annulene links, was obtained from a tellurium‐containing precursor meso‐tetraaryl‐26,28‐ditellurasapphyrin 1. The reaction path proceeds through an acid‐promoted tellurium extrusion from 1 yielding directly 2, characterized in a dicationic form by X‐ray crystallography. In solution the neutral macrocycle 2 reveals flexibility typical for annulenes and it exists as a mixture of conformers that differ by the configuration of the annulene fragments, as proven by 1H NMR studies and analyzed by DFT methods. The conformation is controlled by protonation state, the nature of an interacting anion, solvent identity, and by interaction with water.

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Triphyrin catalyzed direct C–H arylation of benzene with aryl halides

Cited by 19 publications

References 31 publications

Initiation in Photoredox C–H Functionalization Reactions. Is Dimsyl Anion a Key Ingredient?

Initiation in Photoredox C–H Functionalization Reactions. Is Dimsyl Anion a Key Ingredient?

Porphyrinoids with Vinylene Bridges

Shaping a Porphyrinoid Frame by Heteroatoms Extrusion: Formation of an Expanded [22]Triphyrin(6.6.0)

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