Palladium-catalyzed C-C bond formation involving aromatic CH activation. X-ray structure of 5-nitro-8-(2[2.2.1]bicycloheptyl)-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene

Bocelli, Gabriele; Catellani, Marta; Chiusoli, Gian Paolo; Larocca, Susanna

doi:10.1016/0022-328x(84)80060-1

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Palladium Migration In Arenes1

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Cited by 17 publications

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“…That Pd could move from one side to the other of a palladacycle (from sp 3 to sp 2 ) had been previously shown in the case of norbornene [130]. The methanobiphenylene derivative reported in Scheme 43 was obtained by reaction of 4-nitrobromobenzene with norbornene in anisole at 105 • C under the catalytic action of Pd(PPh 3 ) 4 and in the presence of KOAc.…”

Section: Palladium Migration In Arenesmentioning

confidence: 91%

Catalytic C–C coupling through C–H arylation of arenes or heteroarenes

Chiusoli

Catellani

Costa

et al. 2010

Coordination Chemistry Reviews

170

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Section: Palladium Migration In Arenesmentioning

confidence: 91%

Catalytic C–C coupling through C–H arylation of arenes or heteroarenes

Chiusoli

Catellani

Costa

et al. 2010

Coordination Chemistry Reviews

170

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“…In this case the product would form a highly strained cyclobutane ring fused to an aryl ring. Although the formation of products such as these is known, they require prolonged heating at higher temperatures 10b,10c. The mechanism of the next step remains under some debate.…”

Section: Resultsmentioning

confidence: 99%

Application of the Palladium‐Catalysed Norbornene‐Assisted Catellani Reaction Towards the Total Synthesis of (+)‐Linoxepin and Isolinoxepin

et al. 2014

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Our ongoing effort towards the development of highly selective transition‐metal‐catalysed C–H activation processes has led to the expansion of the Catellani reaction. In a Pd0/PdII/PdIV‐catalysed domino reaction, an aryl iodide, alkyl iodide and tert‐butyl acrylate were combined to synthesize the carbon framework of the novel lignan (+)‐linoxepin. The enantioselective synthesis highlights the work accomplished in our group and provides an excellent procedure for the reliable and scalable synthesis of architecturally complex scaffolds. This report outlines the synthetic approaches towards this interesting class of biologically active molecules. After the key Catellani/Heck reaction, our synthesis features a Leimeux–Johnson oxidation and a titanium tetrachloride mediated aldol condensation. Finally, a tuneable Mizoroki–Heck reaction was performed to furnish not only the natural product (+)‐linoxepin but also its isoform, which we have named isolinoxepin.

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