(Phenyl)[o-(trimethylsilyl)phenyl]iodonium triflate. A new and efficient precursor of benzyne

Kitamura, Tsugio; Yamane, Masaji

doi:10.1039/c39950000983

Cited by 115 publications

(64 citation statements)

References 5 publications

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“…[3] Aryne formation of benzoxadisilole by phenyliodination with o-bis(trimethylsilyl)benzene was also reported by Kitamura and Yamane. [11] Recently, we have become interested in the chemistry of arynes generated from benzobis(oxadisilole), benzotris(oxadisilole) and 2,3-naphthoxadisilole under very mild conditions. We found that benzobis(oxadisiloles) could serve as the synthetic equivalent of benzdiynes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Study of Oxadisilole‐Fused Benzisoxazoles or Naphthisoxazoles

Chen

Zhang

et al. 2012

Eur J Org Chem

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Oxadisilole‐fused benzisoxazoles or naphthisoxazoles were obtained through 1,3‐dipolar cycloaddition of arynes with nitrile oxides in good yields at room temperature. Key to the procedure is the simultaneous in situ generation of reactive nitrile oxides from arenecarbohydroximoyl chlorides and aryne reactants from benzobis(oxadisilole) or 2,3‐naphthoxadisilole. One oxadisilole‐fused benzisoxazole is a new precursor of a benzyne formed by a phenyliodination/fluoride‐induced elimination protocol. By using this benzyne, cycloadducts were synthesized in good yields. The de‐oxadisilole reaction of some of the oxadisilole‐fused benzisoxazoles could be easily conducted with a 1.0 M solution of tetrabutylammonium fluoride in THF at room temperature.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Study of Oxadisilole‐Fused Benzisoxazoles or Naphthisoxazoles

Chen

Zhang

et al. 2012

Eur J Org Chem

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“…The two phases were separated and the aqueous phase was extracted with hexane (2 20 mL). The combined organic layers were washed with water (4 20 mL), dried over anhydrous MgSO 4 , filtered, and all volatiles were removed from the filtrate under vacuum. The remaining orange oil was fractionally distilled under reduced pressure (60-65 8C, 10 À2 Torr) to afford 1 as a colorless oil; yield: 5.69 g (62%).…”

Section: Synthesis Of 12-bis(trimethylsilyl)benzene (1) Via Mg Ementioning

confidence: 99%

“…Compound 1 is the key starting material for the synthesis of (i) (phenyl) [2-(trimethylsilyl)phenyl]iodonium triflate (A; Scheme 1), one of the most efficient benzyne precursors available to date, [4,5] (ii) 9,10-dihydro-9,10-diboraanthracene (B; Scheme 1), a versatile building block of luminescent boron-doped p-conjugated polymers, [6,7] and (iii) 9,10-dimethyl-9,10-dihydro-9,10-diboraanthracene, a powerful ditopic LewisScheme 1. 1,2-Bis(trimethylsilyl)benzene (1) is a key starting material for the preparation of the benzyne precursor A, the polymer building block B, and Lewis-acid catalysts C. (i) cf.…”

Section: Introductionmentioning

confidence: 99%

Improved Synthesis of 1,2‐Bis(trimethylsilyl)benzenes using Rieke‐Magnesium or the Entrainment Method

Lorbach¹,

Reus²,

Bolte³

et al. 2010

Adv Synth Catal

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1,2-Bis(trimethylsilyl)benzene is the key starting material for the synthesis of efficient benzyne precursors and certain luminescent p-conjugated materials. We now report that it can be conveniently prepared in tetrahydrofuran from 1,2-dibromobenzene, chlorotrimethylsilane, and either Rieke-magnesium (Mg R ) or magnesium turnings in the presence of 1,2-dibromoethane as an entrainer (Mg e ). The most important advantages of these new protocols over the currently best-established procedure (1,2-dichlorobenzene, chlorotrimethylsilane, magnesium turnings, hexamethylphosphoramide) lie in the milder reaction conditions (Mg R : 08C, 2 h; Mg e : room temperature, 30 min vs. 100 8C, 2 days) and in the fact that the cancerogenic solvent hexa-A C H T U N G T R E N N U N G methylphosphoramide is avoided. Moreover, the improved protocols are also applicable for the highyield synthesis of 1,2,4,5-tetrakis(trimethylsilyl)benzene, 4-fluoro-1,2-bis(trimethylsilyl)benzene, 4-chloro-1,2-bis(trimethylsilyl)benzene, and 4,5-dichloro-1,2-bis(trimethylsilyl)benzene.

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“…A milder method of benzyne generation, starting from 1,4-epoxy-6,7-bis(trimethylsilyl)-1,4-dihydronaphthalene adduct 20 [25] with use of the hypervalent iodine reagent iodobenzene diacetate [PhI(OAc) 2 [26] ], was therefore employed (Scheme 3). The adduct 20 was prepared in two-step fashion from 1,2,4,5-tetrakis(trimethylsilyl)benzene 18.…”

Section: Synthetic Studies Towards Heteronuclear Bis-metallated Systemsmentioning

confidence: 99%

High‐Pressure Assisted Synthesis of Fused Norbornenes Containing Two7‐Metallonorbornene Units

et al. 2005

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The high‐pressure synthesis of new rod‐like and U‐shaped polycyclic compounds containing two 7‐metallonorbornene (silicon or germanium) units fused to the 7‐oxanorbornene rings is described. In addition, the structural features of adduct 9 established by X‐ray structure determination and DFT calculations of model compounds are discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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(Phenyl)[o-(trimethylsilyl)phenyl]iodonium triflate. A new and efficient precursor of benzyne

Cited by 115 publications

References 5 publications

Synthesis and Study of Oxadisilole‐Fused Benzisoxazoles or Naphthisoxazoles

Synthesis and Study of Oxadisilole‐Fused Benzisoxazoles or Naphthisoxazoles

Improved Synthesis of 1,2‐Bis(trimethylsilyl)benzenes using Rieke‐Magnesium or the Entrainment Method

High‐Pressure Assisted Synthesis of Fused Norbornenes Containing Two7‐Metallonorbornene Units

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