Journal ArticleDOI
A highly efficient palladacycle catalyst for hydrophenylation of C-, N-, and O-substituted bicyclic alkenes under aerobic condition.
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TLDR
A new phosphine-free palladacycle catalyst 4 was prepared from benzyl oxazoline in high yield and fully characterized, and hydrophenylation reactions of a wide range of bicyclic alkenes, not only norbornene and norbornadiene but also oxa- and aza-bicyclic al Kenes proceeded smoothly under aerobic condition without exclusion of water.Abstract:
A new phosphine-free palladacycle catalyst 4 was prepared from benzyl oxazoline in high yield and fully characterized. With it as catalyst, hydrophenylation reactions of a wide range of bicyclic alkenes, not only norbornene and norbornadiene but also oxa- and aza-bicyclic alkenes, with iodobenzene proceeded smoothly under aerobic condition without exclusion of water. Up to 1.7 x 10(6) TON as well as 1.2 x 10(5) TOF were achieved.read more
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A rhodium IBiox[(-)-menthyl] complex as a highly selective catalyst for the asymmetric hydroarylation of azabicyles: an alternative route to epibatidine
Jason Bexrud,Mark Lautens +1 more
TL;DR: The synthesis and characterization of a new chiral rhodium N-heterocyclic carbene complex, Rh(IBiox[(-)-menthyl](CO)(2)Cl, is reported and the very high enantioselectivity exhibited by this complex, as a catalyst for the asymmetric hydroarylation of azabicycles, is demonstrated and applied to the synthesis of epibatidine.
Journal ArticleDOI
Asymmetric Ring-Opening Reaction of Oxabicyclic Alkenes with Aryl Boronic Acids Catalyzed by P-Containing Palladacycles
TL;DR: The chiral phosphine-containing palladacycle, synthesized easily from H-MOP, showed its high catalytic activity as well as asymmetric induction ability in ring-opening reaction of oxabicyclic alkenes with arylboronic acids, providing corresponding products in high yields and high ee.
Journal ArticleDOI
Diastereoselective Carbometalation of Oxa- and Azabicyclic Alkenes under Iron Catalysis†
TL;DR: In the presence of catalytic amounts of FeCl3 and diphosphine ligand PDP, oxa- or aza-bridged dihydronaphthalenes, oxabicycle (XIV) or trioxasilatricycle (XVI) are metalated by diarylzinc compounds, which are prepared from ZnCl2 and arylmagnesium bromides prior the reaction as mentioned in this paper.
Journal ArticleDOI
Cobalt‐Catalyzed Allylation of Heterobicyclic Alkenes: Ligand‐Induced Divergent Reactivities
TL;DR: An unprecedented formal hydroallylation of the bicyclic alkenes is realized in high efficiency by using an inexpensive cobalt salt as the catalyst and easy-to-handle potassium allyltrifluoroborate as the reagent.
Journal ArticleDOI
Synthesis of planar chiral [2.2]paracyclophane monophosphine ligands and their application in the umpolung allylation of aldehydes
TL;DR: Chiral [2.2]paracyclophane monophosphines 8 were synthesized via resolution using chiral palladacycle 10 as mentioned in this paper, and they were used as ligands in the umpolung allylation of aldehydes 14 with cyclohexenyl acetate 15, giving homoallyl alcohols 16 in high diastereoselectivity and in moderate to good enantioselectivities.
References
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Journal ArticleDOI
Fine Feathers Make Fine Birds: The Heck Reaction in Modern Garb†
Armin de Meijere,Frank E. Meyer +1 more
TL;DR: The Heck reaction has been a topic of fluctuating interest; however, in the last six years activity in this area has flourished as discussed by the authors, leading to impressive sequences consisting of even different reaction types that occur not only in a consecutive mode, but also in a single operation.
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Palladacycles as Structurally Defined Catalysts for the Heck Olefination of Chloro‐ and Bromoarenes
Wolfgang A. Herrmann,Christoph Brossmer,Karl Öfele,Claus-Peter Reisinger,Thomas Priermeier,Matthias Beller,Hartmut Fischer +6 more
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Application of palladacycles in Heck type reactions
TL;DR: In the last three years, there have been tremendous developments in palladium catalytic systems for Heck type reactions as mentioned in this paper, and one of the successful approaches towards activation of less reactive substrates like aryl chlorides involves the use of palladacycles 1, 2 and 3 as catalyst precursors.
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Asymmetric Catalysis with Chiral Ferrocene Ligands
TL;DR: The advantages of using ferrocene as a scaffold for chiral ligands are described, particularly those regarding planar chirality, rigid bulkiness, and ease of derivatization.