Stoichiometric reactions of nonconjugated dienes with zirconocene derivatives. Further delineation of the scope of bicyclization and observation of novel multipositional alkene regioisomerization

Negishi, Ei‐ichi; Maye, John Paul; Choueiry, Danièle

doi:10.1016/0040-4020(94)01132-j

Cited by 42 publications

(19 citation statements)

References 42 publications

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“…Presumably, anti-disposition of two five-membered rings, each of which is cis-fused onto the zirconacyclopentane ring must be thermodynamically most favorable. 110 A similar preference for cis fusion has also been observed in the construction of the dendrobine skeleton. 83 A recent study has revealed that the Cp 2 Zr-promoted bicyclization of trienes with an internal (Z)-alkene moiety gives predominantly the cis-fused products under the thermodynamically controlled condition.…”

Section: Zr-promoted Intermolecular Coupling Of Alkenes And/or Alkynesmentioning

confidence: 53%

A quarter of a century of explorations in organozirconium chemistry

Negishi

2005

Dalton Trans.

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114

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Systematic explorations of organozirconium chemistry over the past quarter of a century have led to the discoveries and development as well as structural and mechanistic clarifications of novel Zr-catalyzed and -promoted carbon-carbon bond-forming reactions including (i) Ni- or Pd-catalyzed cross-coupling reaction of organozirconiums, (ii) Zr-catalyzed carboalumination of alkynes, (iii) Zr-catalyzed asymmetric carboalumination of alkenes, (iv) generation and carbometallative ring expansion of zirconacyclopropanes and zirconacyclopropenes and a myriad of their transformations and (v) various organozirconium migratory insertion reactions.

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Section: Zr-promoted Intermolecular Coupling Of Alkenes And/or Alkynesmentioning

confidence: 53%

A quarter of a century of explorations in organozirconium chemistry

Negishi

2005

Dalton Trans.

Self Cite

114

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“…Our protocol is efficient toward substrates with electron-withdrawing functional groups such as ketone or ester (14,15), the pharmaceutically relevant trifluoromethyl, and potentially coordinating amine groups (16,17). Functional groups that are frequently reactive in typical precious-metal catalysis-e.g., nitrile (20), bromide (13), or boronic ester (23)-were also tolerated (Fig.…”

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confidence: 99%

E -Olefins through intramolecular radical relocation

Kapat

Sperger

Guven

et al. 2019

Science

149

114

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Full control over the selectivity of carbon–carbon double-bond migrations would enable access to stereochemically defined olefins that are central to the pharmaceutical, food, fragrance, materials, and petrochemical arenas. The vast majority of double-bond migrations investigated over the past 60 years capitalize on precious-metal hydrides that are frequently associated with reversible equilibria, hydrogen scrambling, incompleteE/Zstereoselection, and/or high cost. Here, we report a fundamentally different, radical-based approach. We showcase a nonprecious, reductant-free, and atom-economical nickel (Ni)(I)-catalyzed intramolecular 1,3-hydrogen atom relocation to yieldE-olefins within 3 hours at room temperature. Remote installations ofE-olefins over extended distances are also demonstrated.

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“…65 As illustrated in Scheme 25A, simple unsaturated hydrocarbon substrates containing substituted alkenes rapidly isomerize to conjugated dienes rather than undergoing cyclization. Interestingly, it has been demonstrated that substitution in the tether between the two alkenes can result in regaining the ability to accomplish cyclization.…”

Section: Substrate Scope Limitations In Zr-promoted Diene Cyclizationmentioning

confidence: 99%

5.34 Early Transition Metal Mediated Reductive Coupling Reactions

Micalizio¹

2014

Comprehensive Organic Synthesis II

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Stoichiometric reactions of nonconjugated dienes with zirconocene derivatives. Further delineation of the scope of bicyclization and observation of novel multipositional alkene regioisomerization

Cited by 42 publications

References 42 publications

A quarter of a century of explorations in organozirconium chemistry

A quarter of a century of explorations in organozirconium chemistry

E -Olefins through intramolecular radical relocation

5.34 Early Transition Metal Mediated Reductive Coupling Reactions

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