Synthesis ofo-Dialkenylbenzenes and Indenes Using Heck and Oxypalladation Reactions

Bräse, Stefan; Rümper, Jörg; Voigt, K.; Albecq, Stephane; Thurau, Gert; Villard, Renaud; Waegell, B.; Meijere, Armin de

doi:10.1002/(sici)1099-0690(199804)1998:4<671::aid-ejoc671>3.0.co;2-r

Cited by 33 publications

(15 citation statements)

References 37 publications

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“…[15] Die Anellierung des Triflats 21 mit cyclischen Alkenen beginnt mit einer enantioselektiven intermolekularen Heck-Reaktion gefolgt von einer diastereoselektiven Heck-Cyclisierung (21!22-25, Schema 5). [15] Die Anellierung des Triflats 21 mit cyclischen Alkenen beginnt mit einer enantioselektiven intermolekularen Heck-Reaktion gefolgt von einer diastereoselektiven Heck-Cyclisierung (21!22-25, Schema 5).…”

Section: Methodsunclassified

Brandaktuelles von der enantioselektiven intermolekularen Heck‐Reaktion

Oestreich

2014

Angewandte Chemie

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Die Heck-Reaktion ist eine der grundlegenden Palladium(0)-katalysierten C-C-Bindungsknüpfungsreaktionen, und ihre Bedeutung für die Art und Weise, wie Moleküle heutzutage aufgebaut werden, wurde mit dem Nobelpreis für Chemie ausgezeichnet. Die Breite und der Tiefgang der Forschung, die ihrem Facettenreichtum über die Jahrzehnte gewidmet wurde, [1] hinterlässt die irrige Annahme, dass Heck-Chemie jetzt ein ausgereiftes Gebiet ist. Das mechanistische Verständnis, auf welche Weise die zahllosen Parameter einer Heck-Reaktion deren Ergebnis beeinflussen, ist noch immer unterentwickelt, was auch die undurchsichtigen Faktoren betrifft, die die Regioselektivität der Alkeninsertion sowie der b-Hydrideliminierung bestimmen. Deutlich werden diese Aspekte besonders in intermolekularen Szenarien mit internen (sterisch und elektronisch unvoreingenommenen) Alkenen. Das Unvermçgen, diese Schritte vorhersagbar zu kontrollieren, ist vermutlich für den überschaubaren Fortschritt bei der asymmetrischen Variante verantwortlich. Enantioselektive intermolekulare Heck-Reaktionen bedürfen normalerweise cyclischer Alkene, bei denen konformative Starrheit und folglich eingeschränkte Drehung um C-C-Bindungen die b-Hydrideliminierung von der neu geknüpften C-C-Bindung weg lenkt (Abbildung 1, links). Diese offenkundige Einschränkung wurde jüngst von Sigman und Mitarbeitern mit dem Design von Liganden überwunden, die es er-

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Section: Methodsunclassified

Brandaktuelles von der enantioselektiven intermolekularen Heck‐Reaktion

Oestreich

2014

Angewandte Chemie

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“…A beautiful application of Zhou’s catalytic setup is an asymmetric version of a domino reaction initially devised by de Meijere and co‐workers 15. The annulation of triflate 21 with cyclic alkenes commences with an enantioselective intermolecular Heck reaction followed by a diastereoselective Heck cyclization ( 21 → 22 – 25 , Scheme ) 6.…”

Section: Methodsmentioning

confidence: 99%

2, 6‐Bis((E)‐((5‐benzoyl‐2‐thioxo‐4‐phenylpyrimidin‐1(2H)‐yl)imino)methyl)‐4‐(methyl)phenol and its Metal(II) Complexes: Synthesis, Spectroscopy, Biological Activity, and Photoluminescence Features

Gülcan

Zengin

Çelebı

et al. 2013

Zeitschrift anorg allge chemie

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The preparation, characterization, magnetic measurements, antimicrobial activity, and photoluminescence properties of a number of metal complexes with a Schiff base ligand derived from 2, 6‐diformyl‐4‐methylphenol and 1‐amino‐5‐benzoyl‐4‐phenyl‐1H‐pyrimidine‐2‐thione are reported herein. UV/Vis spectra and magnetic measurements infer square planar stereochemistry for PdII and PtII complexes, and octahedral arrangement for the other metal complexes. The compounds results in intense emission (where λmax = 402 nm) upon irradiation by UV light. The photoluminescence quantum yields and long excited‐state lifetimes of the ligand and its complexes were calculated as 42 % and 3.94 ns, respectively. The photoluminescence intensities and quantum yields of metal complexes changed upon complexation with various metal ions. The ligand and its complexes are of interest as organic emitting materials for electroluminescent devices. The complexes were additionally evaluated for in vitro the antimicrobial activity against bacterial and fungal strains. While CuII, CoII, and PtII complexes have good antifungal efficiency against yeast (MICs, 80 μg·mL–1), only the complex [Cu(L)(AcO)]·4H2O had effective and selective antimicrobial activity against all tested microorganisms with MIC values in the range of 40–80 μg·mL–1, except for E. coli ATCC 4230. This study suggests that the complex [Cu(L)(AcO)]·4H2O may be a new potential antimicrobial substance towards bacteria and fungi.

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“…Interestingly, under the classic Heck conditions with phosphine ligand, the reaction gave mainly the noncyclized isomeric products 29 and 30 in 30% and 12% yield, respectively, and only 3% of the cyclized product 31 (Scheme 10). [24] In 2013, Zhou's group further realized the enantioselective inter-intramolecular double Heck cyclization reaction of 2,3dihydrofuran and o-vinylphenyl triflate using (R)-BINAP(O) or (R)-Xyl-SDP(O) as chiral ligand. A variety of fused carbo-and heterocycles 32 were obtained in moderate to good yields and high stereoselectivity (Scheme 11).…”

Section: Inter-intramolecular Double Heck Reactionmentioning

confidence: 99%

Recent Progress in the Consecutive Double Heck Reaction

Kong

2020

Asian J Org Chem

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Group website: http://wqkong.whu.edu.cnAlthough the Heck reaction has been discovered for more than 50 years, there remains significant opportunities for chemists to make new discoveries. The traditional Heck reaction is mainly limited to the arylation of alkenes, but the efficient construction of diverse polycyclic scaffolds bearing an alkenyl functional group in one‐pot operation by consecutive double Heck cyclization has been scarcely investigated. We therefore summarise the recent progress in Pd‐ and Ni‐catalyzed consecutive double Heck cyclization and highlight the enantioselective transformations and their applications in the total synthesis of natural products with congested quaternary carbon stereocenters.

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Synthesis ofo-Dialkenylbenzenes and Indenes Using Heck and Oxypalladation Reactions

Abstract: o‐Bromostyrenes 2‐Br react with various alkenes in the presence of palladium catalysts to give either substituted indene 6 or o‐diethenylbenzene derivatives 3, depending on the reaction conditions. Under oxidative conditions the latter can be cyclized to indene derivatives as well.

Cited by 33 publications

References 37 publications

Brandaktuelles von der enantioselektiven intermolekularen Heck‐Reaktion

Brandaktuelles von der enantioselektiven intermolekularen Heck‐Reaktion

2, 6‐Bis((E)‐((5‐benzoyl‐2‐thioxo‐4‐phenylpyrimidin‐1(2H)‐yl)imino)methyl)‐4‐(methyl)phenol and its Metal(II) Complexes: Synthesis, Spectroscopy, Biological Activity, and Photoluminescence Features

Recent Progress in the Consecutive Double Heck Reaction

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