Intramolecular and intermolecular oxidative coupling reactions by a new iron complex [Fe(DMF)3Cl2][FeCl4]

Tobinaga, Seisho; Kotani, Eiichi

doi:10.1021/ja00756a071

Cited by 82 publications

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“…The synthesis begins by condensing indole malonate 63 and 2-bromo-3-piperidone 64 in DMF to form indole derivative 65 . Tetracyclic ketone 66 is then generated in one step by sequential reaction of intermediate 65 with 3.2 equiv of LDA and 3.5 equiv of the iron complex [Fe(DMF) 3 Cl 2 ][FeCl 4 ] 77. Although the oxidative coupling of enolates and oxidative cyclization of two enolates was first described in 1977,78 this reaction has been underutilized in complex molecule construction 79.…”

Section: The Aza-cope–mannich Reactionmentioning

confidence: 99%

Molecular rearrangements in the construction of complex molecules

Overman

2009

Tetrahedron

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Section: The Aza-cope–mannich Reactionmentioning

confidence: 99%

Molecular rearrangements in the construction of complex molecules

Overman

2009

Tetrahedron

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“…19 Tobinaga and Kotani performed intermolecular oxidative phenol ether couplings with a well-defined iron complex prepared from FeCl 3 and DMF. 20 Thus, in a water-diethyl ether mixture a 10-fold excess of [Fe(DMF) 3 Cl 2 ][FeCl 4 ] dimerised p-cresol (6) to give Pummerer's ketone 7 in 28% yield (Scheme 2). In intramolecular couplings higher yields have been observed (see below).…”

Section: Introductionmentioning

confidence: 99%

Iron(iii) chloride in oxidative C–C coupling reactions

2009

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In this critical review, the use of iron(III) chloride in oxidative C-C couplings of arenes and related unsaturated compounds is presented and reviewed. The approach allows highly selective dimerisations of phenol derivatives, naphthols, and heterocyclic compounds. Sequential couplings give access to structurally well-defined oligo- and polymers. Iron(III) chloride is commercially available and inexpensive. Being a mild oxidising agent it has been applied in numerous reactions leading to new carbon-carbon-bonds in complex molecular arrays (107 references).

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“…nicht belegbar. 2 s und Trichlorcyclopropenylium-tetrachloroaluminat (9) liefern das Triazulenylcyclopropenylium-Salz 12. ojar die Struktureigenschaften der Azulene und der Azulenium-Verbindungen und iiber weitere elektrochemische Eigenschaften wird berichtet.…”

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“…C 83.60 H 5.26 Gef. C 83.16 H 5.28 1350, 1300, 1290, 1068 1',4,4'- Tetramethoxy-2,2',3,3'-tetramethyl-f 0,lO-bibenz[a] (s, 6H, CH3), 2.85 (s, 6H,1,, 4.03 (s, 6H,4,6H,6,7,8,7.40(dm,J = 11 Hz,2H,9,2H, S,5'-Dimethoxy-ll,ll'-binaphth/2,3-a] ', 1595, 1570, 1515, 870, 740. - Chem.…”

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confidence: 99%

“…164 bis 166°C. -IR (KBr): 3010 cm- ', 2930,1610,1590,1575,1340,1295, ',2',7'-H), 6.37 (m, 2H, 3',6-H), 6.51 (m, l H , 9-H), 6.78 (m, 4H, 7,8,4',5'-H) Umsetzung von 2a rnit Trichlorcyclopropenylium-tetrachloroalurninat (9): Zu einer Suspension aus 412 mg (3.09 mmol) Aluminiumchlorid und 15.0 ml Dichlormethan tropft man unter Wasser-ausschluJ3 und Stickstoff eine Losung von 500 mg (2.81 mmol) Tetrachlorcyclopropen in 3.00 ml Dichlormethan*). Die Mischung wird 15 min bei Raumtemp.…”

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Elektronentransferreaktionen nichtalternierender chinoider und hydrochinoider Verbindungen Verhalten von 5,12‐Dimethoxynaphth[2,3‐a]azulen bei der Oxidation¹⁾

Bindl

Seitz

et al. 1987

Chem. Ber.

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Chirai 5,5',19,12'-tetramethoxy-l 1,ll'-binapbth-(2,3-a]azt~lcne (3a) is formed by oxidative coupling of Za with iron(l1l) chloride in dimethylfonnamide. The reaction of 2a with tropylium tetrafluoroborate (8), triphenylcarbenium salts 7, or trichlorwyclopropenylium tetrachloroaluminate (9) yields either biazulene 3a or electrophilic substitution at C-11, depending on the specific reaction conditions. In case of Za and 8 the azulenium lob, formed in the primary step, is transformed into 11 by reaction with triethylamine. Without base thc formation of biazulene 3r by a SET mechanism via radical cation 18 as intermediate is favored. 7 behaves similar, however, because of steric and electronic reasons an SE reaction could not be observed. Triazulenylcyclopropenylium perchlorate 12 is obtained by the reaction of 2a with 9. Structural details of the newly formed azulenes, biazulenes, and azulenium compounds are discussed with specific considerations of electrochemical and UV/VlS spectral propcrtics.Eigenschaften dieser Verbindungsklasse gehort und seine Ursache in der nichtalternierenden topologischen Struktur von 1 und 2 zu suchen ist, konnte ahnliches Verhalten bei Elektroneniibertragung im oxidativen Bereich erwartet werden. Der Hydrochinon-dimethylether 2a ist geeignet dies zu priifen. Die cyclovoltammetrischen Untersuchungen werden durch Diinnschicht-Spektroelektrochemie (thin layer spectroelectrochemistry) mit Hilfe optisch-transparenter Diinnschichtelektroden (OTTLE) erganzt. Damit wird die Strukturinterpretation der Zwischenstufen durch UV/VIS-Spektren ermoglicht. Praparative Umsetzungen erfolgen sowohl Chem.

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Intramolecular and intermolecular oxidative coupling reactions by a new iron complex [Fe(DMF)3Cl2][FeCl4]

Cited by 82 publications

References 0 publications

Molecular rearrangements in the construction of complex molecules

Molecular rearrangements in the construction of complex molecules

Iron(iii) chloride in oxidative C–C coupling reactions

Elektronentransferreaktionen nichtalternierender chinoider und hydrochinoider Verbindungen Verhalten von 5,12‐Dimethoxynaphth[2,3‐a]azulen bei der Oxidation¹⁾

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Intramolecular and intermolecular oxidative coupling reactions by a new iron complex [Fe(DMF)3Cl2][FeCl4]

Cited by 82 publications

References 0 publications

Molecular rearrangements in the construction of complex molecules

Molecular rearrangements in the construction of complex molecules

Iron(iii) chloride in oxidative C–C coupling reactions

Elektronentransferreaktionen nichtalternierender chinoider und hydrochinoider Verbindungen Verhalten von 5,12‐Dimethoxynaphth[2,3‐a]azulen bei der Oxidation1)

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Elektronentransferreaktionen nichtalternierender chinoider und hydrochinoider Verbindungen Verhalten von 5,12‐Dimethoxynaphth[2,3‐a]azulen bei der Oxidation¹⁾