Catalytic Stereospecific Allyl–Allyl Cross-Coupling of Internal Allyl Electrophiles with AllylB(pin)
نویسندگان
چکیده
منابع مشابه
Catalytic Stereospecific Allyl–Allyl Cross-Coupling of Internal Allyl Electrophiles with AllylB(pin)
Application of internal electrophiles in catalytic stereospecific allyl-allyl cross-coupling enable the rapid construction of multisubstituted 1,5-dienes, including those with all carbon quaternary centers. Compounds with minimal steric differentiation can be synthesized with high enantiomeric excess.
متن کاملCatalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles
As part of our ongoing effort to expand the scope of cross-coupling reactions of alkyl electrophiles, we have pursued a strategy wherein the nucleophilic coupling partner includes a pendant olefin; after transmetalation by such a substrate, if β-migratory insertion proceeds faster than direct cross-coupling, an additional carbon-carbon bond and stereocenter can be formed. With the aid of a nick...
متن کاملAnalysis of key steps in the catalytic cross-coupling of alkyl electrophiles under Negishi-like conditions.
The use of tpy'(tpy'= 4,4',4''-tri-tert-butyl-terpyridine) as a ligand for nickel allows for the isolation of a Ni(I)-alkyl complex and a Ni(II)-alkyl halide complex, both of which can be used as mechanistic probes of key steps in alkyl cross-coupling reactions.
متن کاملCatalytic intermolecular allyl-allyl cross-couplings between alcohols and boronates.
We developed catalytic intermolecular C(sp(3))-C(sp(3)) cross-couplings between various allyl alcohols and allyl boronates, which proceeded smoothly in the presence of nickel(0) under mild conditions to form 1,5-dienes with excellent linear- and γ-selectivity; the use of boronates proved to be crucial in terms of reactivity.
متن کاملEvidence for a NiI active species in the catalytic cross-coupling of alkyl electrophiles.
Addition of terpyridine to (TMEDA)Ni(CH3)2 results in the high-yield formation of (terpyridyl)NiMe (3). This NiI organometallic complex was found to be capable of transferring its methyl group to iodocyclohexane to produce methylcyclohexane in high yield. Compound 3 can also serve as an initiator for the catalytic cross-coupling of alkyl electrophiles performed under Negishi-like conditions.
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2014
ISSN: 1523-7060,1523-7052
DOI: 10.1021/ol500456s