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Literature DB >> 12769566

Palladium-catalyzed bissilylation of arynes with cyclic disilanes: synthesis of benzo-annulated disilacarbocycles.

Hiroto Yoshida¹, Junnai Ikadai, Miwa Shudo, Joji Ohshita, Atsutaka Kunai.

Abstract

Arynes, generated in situ from 2-(trimethylsilyl)aryl triflate and a fluoride ion, were found to insert into a silicon-silicon bond of cyclic disilanes in the presence of a catalytic amount of a palladium-tert-alkyl isocyanide complex to afford diverse benzo-annulated disilacarbocycles straightforwardly in modest to high yields.

Entities: Chemical

Year: 2003 PMID： 12769566 DOI： 10.1021/ja034571d

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

9 in total

1. Facile N-arylation of amines and sulfonamides and o-arylation of phenols and arenecarboxylic acids.

Authors: Zhijian Liu; Richard C Larock
Journal: J Org Chem Date: 2006-04-14 Impact factor: 4.354

2. Synthesis of 2H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes.

Authors: Yuesi Fang; Chunrui Wu; Richard C Larock; Feng Shi
Journal: J Org Chem Date: 2011-10-12 Impact factor: 4.354

3. Synthesis of benzisoxazolines by the coupling of arynes with nitrones.

Authors: Chun Lu; Anton V Dubrovskiy; Richard C Larock
Journal: J Org Chem Date: 2012-02-16 Impact factor: 4.354

4. π-Extension of heterocycles via a Pd-catalyzed heterocyclic aryne annulation: π-extended donors for TADF emitters.

Authors: Katie A Spence; Jason V Chari; Mattia Di Niro; Robert B Susick; Narcisse Ukwitegetse; Peter I Djurovich; Mark E Thompson; Neil K Garg
Journal: Chem Sci Date: 2022-05-04 Impact factor: 9.969

5. Sequential cycloaddition and ring expansion reaction of arynes and methylenebenzothiopheneones: synthesis of a benzo-fused eight-membered ring via sulfonium ylides.

Authors: Peng Xiao; Shikuan Su; Wei Wang; Weiguo Cao; Jie Chen; Jian Li; Yali Chen
Journal: RSC Adv Date: 2019-11-29 Impact factor: 3.361

Palladium-catalyzed bissilylation of arynes with cyclic disilanes: synthesis of benzo-annulated disilacarbocycles.

1. Facile N-arylation of amines and sulfonamides and o-arylation of phenols and arenecarboxylic acids.

2. Synthesis of 2H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes.

3. Synthesis of benzisoxazolines by the coupling of arynes with nitrones.

4. π-Extension of heterocycles via a Pd-catalyzed heterocyclic aryne annulation: π-extended donors for TADF emitters.

5. Sequential cycloaddition and ring expansion reaction of arynes and methylenebenzothiopheneones: synthesis of a benzo-fused eight-membered ring via sulfonium ylides.

6. Copper Catalysis for Synthesizing Main-Group Organometallics Containing B, Sn or Si.

7. Bis-silylation of internal alkynes enabled by Ni(0) catalysis.

8. Arynes as Radical Acceptors: TEMPO-Mediated Cascades Comprising Addition, Cyclization, and Trapping.

9. A platform for on-the-complex annulation reactions with transient aryne intermediates.