Cobalt-catalyzed [2 + 2 + 2] cycloaddition copolymerization of diyne and internal alkyne monomers to highly branched polymers

Kikuta, Nana; Shindo, Takahiro; Sugiyama, Yu‐ki; Yamada, Takeshi; Okamoto, Sentaro

doi:10.1016/j.polymer.2020.123133

Cited by 6 publications

(2 citation statements)

References 27 publications

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“…In the course of our studies on alkyne transformations catalysed by transition-metal complexes, [25][26][27] we found that 1,6diyne compound 1 reacts in the presence of a 2-(2,6-diiso-propylphenyl)iminomethylpyridine (dipimp)/NiCl 2 -6H 2 O/Zn catalyst to produce a polymeric material accompanied by COT compound 4 and the corresponding benzene derivatives (Scheme 1). 13 Then, optimisation of the reaction conditions to attain a high yield of the polymeric material by minimising the formation of 4 and the benzene derivatives enabled us to conduct the polymerisation of 1 in a controlled manner to yield medium-size cyclic polyenes 2 (Scheme 1) with narrow polydispersity indices (PDIs).…”

Section: Resultsmentioning

confidence: 99%

Nickel-catalysed cycloaddition oligomerisation of 1,6-diynes to medium-size cyclic polyenes

2022

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Section: Resultsmentioning

confidence: 99%

Nickel-catalysed cycloaddition oligomerisation of 1,6-diynes to medium-size cyclic polyenes

2022

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“…Nevertheless, polycyclotrimerizations of internal alkynes have been rarely employed to prepare HBPs. [34][35][36] This is mainly caused by the low reactivity and high steric hindrance of internal alkynes. Recently, we have developed a rhodium-catalyzed polycyclotrimerization of diphenylpropiolates for the synthesis of ester-functionalized HBPs.…”

Section: Introductionmentioning

confidence: 99%

Metal-free polycyclotrimerization of trimethylsilyl-protected diynes: a facile strategy toward regioregular hyperbranched polyarylenes

et al. 2023

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Cobalt‐Catalyzed [2 + 2 + 2] Cycloaddition Reactions

Glasel,

Hapke

2023

Patai's Chemistry of Functional Groups

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Cobalt‐catalyzed [2 + 2 + 2] cycloaddition reactions are an important tool for the assembly of carbo‐ and hetero‐cyclic ring systems from simple precursor molecules such as alkynes, alkenes, nitriles, and other heterocumulenes such as isocyanates. Cyclopentadienyl (Cp)‐cobalt complexes are still one of the most important classes of catalysts, but in situ generated cobalt catalyst systems are becoming increasingly important for the assembly of achiral as well as chiral target molecules from a large variety of substrates. Substrates comprise simple terminal as well as internal alkynes, diynes, and higher oligoynes and also allow target‐oriented syntheses of unusually large as well as highly substituted molecules as well as natural product synthesis with a cyclotrimerization as the key step of the synthetic sequence. The utilization of olefins as cyclization partners allows the synthesis of products with lesser degree of unsaturation such as cyclohexadienes, cyclohexenes, and dihydropyridines, just to name a view examples. Chiral catalyst systems allow the enantioselective synthesis of biaryls and products with central chirality, and chiral starting materials allow the synthesis of diastereomeric helicenes in an efficient manner. Novel catalysts and reaction engineering allow reaction conditions such as conventional thermal or microwave heating, photochemically assisted cyclizations, and the use of plug‐flow reactors.

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Cobalt-catalyzed [2 + 2 + 2] cycloaddition copolymerization of diyne and internal alkyne monomers to highly branched polymers

Cited by 6 publications

References 27 publications

Nickel-catalysed cycloaddition oligomerisation of 1,6-diynes to medium-size cyclic polyenes

Nickel-catalysed cycloaddition oligomerisation of 1,6-diynes to medium-size cyclic polyenes

Metal-free polycyclotrimerization of trimethylsilyl-protected diynes: a facile strategy toward regioregular hyperbranched polyarylenes

Cobalt‐Catalyzed [2 + 2 + 2] Cycloaddition Reactions

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