Co(I)- versus Ru(II)-Catalyzed [2+2+2] cycloadditions involving alkynyl halides

Iannazzo, Laura; Kotera, Naoko; Malacrìa, Max; Aubert, Corinne; Gandon, Vincent

doi:10.1016/j.jorganchem.2011.08.041

Cited by 18 publications

(7 citation statements)

References 21 publications

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“…Cycloaddition of the same diyne with phenylacetylene indicated steric interactions from the methyl groups on the Cp ring increase efficiency but decrease regioselectivity. A related study on the intramolecular [2+2+2] cycloadditions of diiodotriynes was reported by Aubert and Gandon in 2011 (not shown) …”

Section: Six-membered Ring Formationmentioning

confidence: 70%

“…217 Interestingly, in a 2010 kinetic study, Yamamoto investigated the performance of a series of polymethylcyclopentadienyl ruthenium complexes in [2+2+2] cycloadditions 218 cycloadditions of diiodotriynes was reported by Aubert and Gandon in 2011 (not shown). 219 Intramolecular Cp*RuCl(cod)-catalyzed alkyne [2+2+2] cycloadditions of acyclic triynes have been utilized to great effect in the total synthesis of natural products. In 2010, Deiters reported the first total synthesis of the terpenoid cryptoacetalide using a microwave-mediated alkyne [2+2+2] cyclotrimerization to construct the central benzene ring (Scheme 43).…”

Section: [2+2+2]mentioning

confidence: 99%

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Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings

Doerksen

Hodík

et al. 2021

Chem. Rev.

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Ruthenium-catalyzed cycloadditions to form five-, six-, and seven-membered rings are summarized, including applications in natural product total synthesis. Content is organized by ring size and reaction type. Coverage is limited to processes that involve formation of at least one C–C bond. Processes that are stoichiometric in ruthenium or exploit ruthenium as a Lewis acid (without intervention of organometallic intermediates), ring formations that occur through dehydrogenative condensation-reduction, σ-bond activation-initiated annulations that do not result in net reduction of bond multiplicity, and photochemically promoted ruthenium-catalyzed cycloadditions are not covered.

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Section: Six-membered Ring Formationmentioning

confidence: 70%

Section: [2+2+2]mentioning

confidence: 99%

Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings

Doerksen

Hodík

et al. 2021

Chem. Rev.

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“…Inspired by our recent work on cobalt‐catalyzed cycloadditions involving alkynyl halides,9 we envisaged the use of cyanogen bromide as nitrile partner (Scheme ). Although the expected bicyclic aminopyridine was not observed in this case, the unprecedented cyanoynamide 9 was isolated in 38 % yield 10.…”

Section: Resultsmentioning

confidence: 99%

“…This first set of experiments revealed the importance of steric factors in this process. Indeed, whereas the use of acetonitrile furnished 3aminopyridine 2 in 72 % yield, bulky pivalonitrile gave rise to 3 in only 36 % yield ( Inspired by our recent work on cobalt-catalyzed cycloadditions involving alkynyl halides, [9] we envisaged the use of cyanogen bromide as nitrile partner (Scheme 1). Although the expected bicyclic aminopyridine was not observed in this case, the unprecedented cyanoynamide 9 was isolated in 38 % yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Aminopyridines and Aminopyridones by Cobalt‐Catalyzed [2+2+2] Cycloadditions Involving Yne‐Ynamides: Scope, Limitations, and Mechanistic Insights

Garcia¹,

Evanno

George

et al. 2012

Chemistry A European J

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An in-depth study of the cobalt-catalyzed [2+2+2] cycloaddition between yne-ynamides and nitriles to afford aminopyridines has been carried out. About 30 nitriles exhibiting a broad range of steric demand and electronic properties have been evaluated, some of which open new perspectives in metal-catalyzed arene formation. In particular, the use of [CpCo(CO)(dmfu)] (dmfu=dimethyl fumarate) as a precatalyst made possible the incorporation of electron-deficient nitriles into the pyridine core. Modification of the substitution pattern at the yne-ynamide allows the regioselectivity to be switched toward 3- or 4-aminopyridines. Application of this synthetic methodology to the construction of the aminopyridone framework using a yne-ynamide and an isocyanate was also briefly examined. DFT computations suggest that 3-aminopyridines are formed by formal [4+2] cycloaddition between the nitrile and the intermediate cobaltacyclopentadiene, whereas 4-aminopyridines arise from an insertion pathway.

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“…The arene rings that were constructed by the [2+2+2] cycloaddition are highlighted in red. Investigations were directed towards the synthesis of functionalised arenes, such as various halo-and bromofunctionalised arenes (136), 259 boron-functionalised arenes (137) 260 and other functional groups prone to polymerisation reactions. 261,262 Also, investigations for the synthesis of extended polycyclic materials, 263 such as 138, star-like polyarenes, 264 or chiral helicenes, 265,266 were reported.…”

Section: Syn Thesis 63 [2+2+2] Cycloadditionmentioning

confidence: 99%

Cobalt-Catalysed Bond Formation Reactions; Part 2

Röse

Hilt

2015

Synthesis

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This review summarises the cobalt-catalysed reactions of the years 2008 through 2014. Covered are addition reactions, such as the hydrogenation of double bonds, the addition of C-H bonds to double and triple bonds, C-H activation reactions, cobalt-catalysed cross-coupling reactions and selected additions of H-B and H-Si bonds to unsaturated starting materials. The cobalt-catalysed cycloadditions range from cyclopropanations, [2+2], Pauson-Khand reactions, [2+2+2], [4+2], [6+2] cycloadditions as well as benzannulations. Also covered are Nicholas reactions, cobalt-catalysed Jacobsen's kinetic resolution of epoxides as well as selected miscellaneous cobalt-catalysed processes mainly for carbon-carbon bond formations. 1 Introduction 2 Addition Reactions 3 Homo-and Cross-Coupling Reactions 4 Jacobsen Kinetic Resolution of Epoxides 5 Nicholas Reactions 6 Cycloaddition Reactions 7 Miscellaneous 8 Conclusion

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Co(I)- versus Ru(II)-Catalyzed [2+2+2] cycloadditions involving alkynyl halides

Cited by 18 publications

References 21 publications

Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings

Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings

Synthesis of Aminopyridines and Aminopyridones by Cobalt‐Catalyzed [2+2+2] Cycloadditions Involving Yne‐Ynamides: Scope, Limitations, and Mechanistic Insights

Cobalt-Catalysed Bond Formation Reactions; Part 2

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