Copper‐mediated Diastereoselective Conjugate Addition and Allylic Substitution Reactions

Breit, Bernhard; Demel, Peter

doi:10.1002/3527600086.ch6

Cited by 34 publications

(15 citation statements)

References 32 publications

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“…In CuRf(tht), the Rf group provides extra stability to the C–Cu bond compared with non-fluorinated aryls , and allows straightforward 19 F nuclear magnetic resonance (NMR) monitoring . The distinctive feature for organometallic copper(I) compounds is the variability in stoichiometries and the structural diversity of its complexes. , Homoleptic compounds, CuR, are usually cyclic oligomers, but copper complexes of stoichiometry [CuRL] show typically linear geometry, similar to gold(I) derivatives. − The only report of linear complexes with tht [CuR(tht)] includes the very encumbered group R: 2,6-bis(2,4,6-triisopropylphenyl)phenyl . Trigonal-planar complexes CuRL 2 and oligomers with several other stoichiometries such as [CuRL 0.5 ] n are also known …”

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[Cu(C₆Cl₂F₃)(tht)]₄: An Extremely Efficient Catalyst for the Aryl Scrambling between Palladium Complexes

2019

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The copper compound [Cu(C6Cl2F3)(tht)]4 (1) (tht: tetrahydrothiophene) is an excellent catalyst for the trans-to cis-isomerization of complexes [PdAr2(tht)2](Ar: fluoroaryl) and also for the exchange of aryls between those palladium complexes. Herein, we also communicate the synthesis and characterization of 1, and some of its derivatives. The x-ray structure of 1 shows a linear chain of copper atoms, supported by fluoroaryl rings. The NMR 19 F-DOSY study indicates that this structure is preserved in solution although in equilibrium with other species. ASSOCIATED CONTENT Supporting Information. The supporting information contains: Experimental and computational methods (11 pages). This material is available free of charge via the Internet at http://pubs.acs.org AUTHOR INFORMATION

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[Cu(C₆Cl₂F₃)(tht)]₄: An Extremely Efficient Catalyst for the Aryl Scrambling between Palladium Complexes

2019

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“…Following on these studies, we decided to investigate the performance of our dual catalytic system in the allylboration of alkynes with cyclic racemic allylic carbonates (Scheme B). Although organocopper reagents have been identified as “soft” nucleophiles in their direct reactions with allylic substrates, little is known about their nucleophilic nature in Pd-catalyzed allylation reactions . While copper enolates have been reported to behave as “soft” nucleophiles in Cu/Pd-catalyzed alkylation of chiral allylic substrates, the behavior of alkenylcopper nucleophiles in this type of reactions is unknown.…”

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Transmetalation as Key Step in the Diastereo- and Enantioselective Synergistic Cu/Pd-Catalyzed Allylboration of Alkynes with Racemic Allylic Carbonates

et al. 2020

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“…The bond between the ferrocenyl p-tolyl sulfoxide and the benzoquinone moiety can be introduced by, for example, copper-catalysed conjugate addition [19] or a metal-mediated cross-coupling reaction. The advantage of conjugate addition is that the quinone is formed in one step.…”

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confidence: 99%

Highly Selective Negishi Cross‐Coupling Reaction of a Zinc‐Metallated Ferrocenyl p‐Tolyl Sulfoxide: New Chiral Ferrocene‐Based Quinone Ligands

2003

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A highly selective Negishi coupling of zinc-metallated ferrocenyl p-tolyl sulfoxide with aryl bromides was developed. With Pd(PPh 3 ) 4 as catalyst, a well-matched system in terms of reactivity of organometallic compound, aryl bromide, and catalyst, was obtained. The scope of the reaction was studied by the use of aryl bromides 7a−g, which afforded high yields of coupling products. The reaction conditions for the preparation of ferrocenyl p-tolyl sulfoxide, according to the Andersen method, were optimised to give a yield of 80% and an enantio-

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Copper‐mediated Diastereoselective Conjugate Addition and Allylic Substitution Reactions

Cited by 34 publications

References 32 publications

[Cu(C₆Cl₂F₃)(tht)]₄: An Extremely Efficient Catalyst for the Aryl Scrambling between Palladium Complexes

[Cu(C₆Cl₂F₃)(tht)]₄: An Extremely Efficient Catalyst for the Aryl Scrambling between Palladium Complexes

Transmetalation as Key Step in the Diastereo- and Enantioselective Synergistic Cu/Pd-Catalyzed Allylboration of Alkynes with Racemic Allylic Carbonates

Highly Selective Negishi Cross‐Coupling Reaction of a Zinc‐Metallated Ferrocenyl p‐Tolyl Sulfoxide: New Chiral Ferrocene‐Based Quinone Ligands

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Copper‐mediated Diastereoselective Conjugate Addition and Allylic Substitution Reactions

Cited by 34 publications

References 32 publications

[Cu(C6Cl2F3)(tht)]4: An Extremely Efficient Catalyst for the Aryl Scrambling between Palladium Complexes

[Cu(C6Cl2F3)(tht)]4: An Extremely Efficient Catalyst for the Aryl Scrambling between Palladium Complexes

Transmetalation as Key Step in the Diastereo- and Enantioselective Synergistic Cu/Pd-Catalyzed Allylboration of Alkynes with Racemic Allylic Carbonates

Highly Selective Negishi Cross‐Coupling Reaction of a Zinc‐Metallated Ferrocenyl p‐Tolyl Sulfoxide: New Chiral Ferrocene‐Based Quinone Ligands

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[Cu(C₆Cl₂F₃)(tht)]₄: An Extremely Efficient Catalyst for the Aryl Scrambling between Palladium Complexes

[Cu(C₆Cl₂F₃)(tht)]₄: An Extremely Efficient Catalyst for the Aryl Scrambling between Palladium Complexes