Diels–Alder Reactions for the Construction of Cyclopropylarenes

Arndt, Marion; Hilt, Gerhard; Khlebnikov, Alexander F.; Kozhushkov, Sergei I.; Meijere, Armin de

doi:10.1002/ejoc.201200105

Cited by 18 publications

(8 citation statements)

References 45 publications

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“…The cyclopropylarenes have also served as starting materials for synthesis of chiral intermediates via enzymatic oxidation 11. They are commonly prepared by cycloaddition of alkynes with dienes12 or cross‐coupling reactions using Suzuki13 or other protocols 14…”

Section: Introductionmentioning

confidence: 99%

[2+2+2]‐Cyclotrimerization of 1‐Cyclopropyl‐1,6‐diynes with Alkynes: Formation of Cyclopropylarenes.

et al. 2016

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Cyclotrimerization of 1-cyclopropyl-1,6diynes with various terminal alkynes wast ested under catalytic conditions using rhodium and ruthenium catalysts.W eo bserved that the regioselectivity of the reaction, that is,f ormation of 1,2-or 1,3-regioisomers,w as opposite for the two metals.F or the ruthenium complex[ Cp*Ru(cod)Cl]-catalyzed reactions the yieldsw ere in many cases high with as trong preference for the formation of 1,3-substituted regioisomers.I nt he case of catalysisb yt he rhodiumc omplex[ RhCl(PPh 3 ) 3 ], 1,2-substituted productsw ere generally preferred, albeit the selectivity waso ften modest.H owever, by changing the ligand environment around the central rhodium atom the regioselectivity as well as yields of the productsw eres ignificantly improved. Fore xample, by using ac ombination of the rhodium complex [Rh(cod) 2 BF 4 ]and 1,4-bis(diphenylphosphino)butane the regioselectivity wasc hanged from 1:1t o1 :12 in favor of the 1,2-regioisomer. This catalytic system was also applied for synthesis of as ubstituted 4-cyclopropyl-3-hydroisobenzofuran-1-one that could serve as ap otential intermediate for preparation of antihypertensivea gents.

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Section: Introductionmentioning

confidence: 99%

[2+2+2]‐Cyclotrimerization of 1‐Cyclopropyl‐1,6‐diynes with Alkynes: Formation of Cyclopropylarenes.

et al. 2016

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“…Besides oxygen‐functionalised 1,3‐dienes, alkynyl sulfur derivatives, amide‐ and imide‐functionalised alkynes, phosphorus‐functionalised alkynes, trimethylsilyl‐modified alkynes, and boron‐functionalised alkynes could also be applied successfully in the cobalt‐catalysed Diels–Alder‐type reaction . Recently, cyclopropyl substituents were placed at various positions of the 1,3‐diene as well as on the alkyne component, and the cobalt‐catalysed Diels–Alder reaction proceeded successfully without ring opening of the cyclopropyl moieties. This result indicates that an electron transfer from the low‐valent cobalt catalyst central atom to the coordinated unsaturated starting materials is unlikely, as ring opening should then have been observed.…”

Section: Methodsmentioning

confidence: 99%

1,4‐Cyclohexadienes—Easy Access to a Versatile Building Block via Transition‐Metal‐Catalysed Diels–Alder Reactions

Hilt

2014

The Chemical Record

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1,4-Cyclohexadiene derivatives are easily accessed via transition-metal cycloadditions of 1,3-dienes with alkynes. The mild reaction conditions of several transition-metal-catalysed reactions allows the incorporation of various functional groups to access functionalised 1,4-cyclohexadienes. The control of the regiochemistry in the intermolecular cobalt-catalysed Diels-Alder reaction is realised utilising different ligand designs. The functionalised 1,4-cyclohexadiene derivatives are valuable building blocks in follow-up transformations. Finally, the oxidation of the 1,4-cyclohexadienes can be accomplished under mild conditions to generate the corresponding arene derivatives.

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“…310 The Hilt group also investigated the application of a number of cyclopropyl-substituted alkynes and 1,3-dienes and in no case was the ringopening of the cyclopropyl-substituent encountered, indicating that a radical character on the alkyne or 1,3-diene when coordinated to the cobalt can be excluded. 311 A considerable improvement of the method was reported by Yoshikai for the cobalt-catalysed aza-Diels-Alder reaction of α,β-unsaturated imines (Scheme 85…”

Section: Scheme 84mentioning

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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Diels–Alder Reactions for the Construction of Cyclopropylarenes

Cited by 18 publications

References 45 publications

[2+2+2]‐Cyclotrimerization of 1‐Cyclopropyl‐1,6‐diynes with Alkynes: Formation of Cyclopropylarenes.

[2+2+2]‐Cyclotrimerization of 1‐Cyclopropyl‐1,6‐diynes with Alkynes: Formation of Cyclopropylarenes.

1,4‐Cyclohexadienes—Easy Access to a Versatile Building Block via Transition‐Metal‐Catalysed Diels–Alder Reactions

Cobalt-Catalysed Bond Formation Reactions; Part 2

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