Ruthenium-catalyzed intramolecular cyclization of hetero-functionalized allylbenzenes

Ohta, Tetsuo; Kataoka, Yohei; Miyoshi, Akio; Oe, Yohei; Furukawa, Isao; Ito, Yoshihiko

doi:10.1016/j.jorganchem.2006.05.059

Cited by 36 publications

(23 citation statements)

References 47 publications

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“…The search for a specific metal catalyst for hydroalkoxylation [4a, 5-7] of nonactivated alkenes, using the reaction of Scheme 1 as a model reaction, was initiated by a 1998 report on a ruthenium triflate catalyst. [18][19][20] Since then, numerous similar reports on catalysis with ZrCl 4 , [21] Sn(OTf) 4 , [22] Al(OTf) 3 , [23] Cu(OTf) 2 or AgOTf, [24] Ln(OTf) 3 in ionic liquids, [25,26] or with Au(PPh 3 )OTf [27] have appeared. Related catalysts were also reported for the tandem conversion of allyl aryl ethers, via 2-allylphenols to coumarans.…”

Section: Introductionmentioning

confidence: 99%

Aluminum‐Catalyzed Hydroalkoxylation at Elevated Temperatures: Fast and Simple Access to Coumarans and Other Oxygen Heterocycles

2013

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An aluminum‐catalyzed intramolecular hydroalkoxylation of nonactivated alkenes is presented as a powerful synthetic tool for the preparation of oxygen heterocycles, which are of major interest for the preparation of biological and pharmaceutical active compounds. The aluminum isopropoxide catalyzed (5 mol %) cyclization of 2‐allylphenols at elevated temperatures (250 °C, 20 min) provides 2‐methylcoumarans (2‐methyl‐2,3‐dihydrobenzofuran) in an exceptionally fast, simple, and economic manner. Moreover, heating of allyl aryl ethers with aluminum isopropoxide (5 mol %) gives 2‐methylcoumarans by a tandem Claisen rearrangement–hydroalkoxylation reaction. For either reaction, the catalyst tolerates a broad scope of substrates with various functional groups. By using the weakly electrophilic aluminum alkoxide as the catalyst, occurrence of “hidden Brønsted acid” catalysis can be excluded under the present reaction conditions.

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Section: Introductionmentioning

confidence: 99%

Aluminum‐Catalyzed Hydroalkoxylation at Elevated Temperatures: Fast and Simple Access to Coumarans and Other Oxygen Heterocycles

2013

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“…No explanation for the role of copper triflate was given; however, it alone did not catalyze the reaction in acetonitrile. Hydrocarboxylation was also demonstrated with the RuCl 3 catalyst system [114].…”

Section: Reactions Of Hydroxyalkenesmentioning

confidence: 93%

“…Later in 2007, the authors expanded the scope of this reaction (Scheme 59) [114,115], and also illustrated that (RuCp*Cl 2 ) 2 in combination with AgOTf was an effective catalyst for the hydroalkoxylation of hydroxyalkenes. The Ru-catalysts gave similar regioselectivities for cyclization as were observed for the Pt-catalysts above.…”

Section: Reactions Of Hydroxyalkenesmentioning

confidence: 99%

Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Hydroamination or Hydroalkoxylation Reactions

Julian

2013

Topics in Heterocyclic Chemistry

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The intramolecular hydrofunctionalization of carbon-carbon multiple bonds has emerged as a powerful way to form cyclic structures. A particularly important class of reactions involves the use of amine or alcohol nucleophiles, and alkenes or allenes as electrophiles, to form pyrrolidine, piperidine, tetrahydrofuran, and tetrahydropyran heterocycles in a highly efficient manner using late transition metal catalysts. Asymmetric methods for hydroamination and hydroalkoxylation reactions have recently emerged, allowing for the enantioselective synthesis of such saturated heterocycles. This review covers recent developments (over the last 5-10 years) in late transition metal-catalyzed hydroamination and hydroalkoxylation reactions that generate saturated heterocycles.

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“…It is speculated that Ru works as a Lewis acid that activates the olefin substrate by forming peolefin complex like Wacker-type reactions [127]. Ru III species; RuCl 3 .nH 2 O/AgOTf also found to be an effective catalyst for this type of reactions [128].…”

Section: Hydroalkoxylation and Hydrocarboxylationmentioning

confidence: 99%

Recent progress in transition metal catalysed hydrofunctionalisation of less activated olefins

Yadav

Antony

Rao

et al. 2011

Journal of Organometallic Chemistry

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Ruthenium-catalyzed intramolecular cyclization of hetero-functionalized allylbenzenes

Cited by 36 publications

References 47 publications

Aluminum‐Catalyzed Hydroalkoxylation at Elevated Temperatures: Fast and Simple Access to Coumarans and Other Oxygen Heterocycles

Aluminum‐Catalyzed Hydroalkoxylation at Elevated Temperatures: Fast and Simple Access to Coumarans and Other Oxygen Heterocycles

Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Hydroamination or Hydroalkoxylation Reactions

Recent progress in transition metal catalysed hydrofunctionalisation of less activated olefins

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