Synthesis of azinoazole structural isomers by photocyclization

Frolov, A. N.

doi:10.1134/s1070428006060121

Cited by 16 publications

(14 citation statements)

References 4 publications

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“…According to the results of the density functional calculations, the values of total energy for derivatives (a) with N Py ǞM bonds are larger than those for the corresponding compounds (b) without these contacts for all species studied. The differences between the energy values for the starting materials lie within the range 7.03 (20) to 35.04 kcal mol -1 (16). The analogous values for the rearrangement products are 5.89 (20) to 41.27 kcal mol -1 (16).…”

Section: Density Functional Study On Metal Complexes and Nucleophilicmentioning

confidence: 90%

“…The differences between the energy values for the starting materials lie within the range 7.03 (20) to 35.04 kcal mol -1 (16). The analogous values for the rearrangement products are 5.89 (20) to 41.27 kcal mol -1 (16). It is of interest to note that the total energy of 9a(fac) is practically identical to that of 9a(mer):…”

Section: Density Functional Study On Metal Complexes and Nucleophilicmentioning

confidence: 90%

“…Ligand 1 was first prepared by treating 2-bromopyridine with (pentafluorophenyl)amine, [16] although recently Ashenhurst et al have used the approach of Koppang for the synthesis of 1, [17] which involves the treatment of C 6 F 6 with an equimolar mixture of (2-pyridylamido)lithium and LiNH 2 . [18] We also used this reaction to prepare amine 1, although we modified the method according to Equation (1).…”

Section: Synthesismentioning

confidence: 99%

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ortho‐Directed Metathetical Fluoride/Amide Exchange in (Pentafluorophenyl)amides

Shutov¹,

Karlov²,

Harms³

et al. 2007

Eur J Inorg Chem

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The indium tris(amide)s [(Et2N)3–nIn{N(C6F5)(2‐C5H4N)}n] [n = 1 (15), 2 (16) or 3 (9)] have been prepared by treatment of [In(NEt2)3]2 (3) with a stoichiometric amount of (2‐C5H4N)(C6F5)NH (1). The analogous reaction of Bi(NMe2)3 (2) with 3 equiv. of amine 1 and the treatment of BiCl3 (5) with a stoichiometric amount of (2‐C5H4N)(C6F5)NLi (4) both lead to [Bi{N(C6F5)(2‐C5H4N)}3] (10). In contrast, only the difluoride 11 or the monofluoride 12, which are the products of intramolecular ortho‐directed exchange of NMe2 and F substituents, are obtained from the reaction of 2 with 1 or 2 equiv. of 1, respectively. The reaction between Me3Sb(Hal)2 [Hal = Br (7) Cl, (8)] and 1 or 2 equiv. of lithium salt 4 gives the corresponding stable monoamides [Me3(Hal)Sb{N(C6F5)(2‐C5H4N)}] [Hal = Br (17), Cl (18)] or bis(amide) [Me3Sb{N(C6F5)(2‐C5H4N)}2] (19), respectively. The structure of 9 has been confirmed by an X‐ray structure analysis, and density functional calculations data have been used to explain the possible reaction pathway of the ortho‐directed metathetical fluoride/amide exchange.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: Density Functional Study On Metal Complexes and Nucleophilicmentioning

confidence: 90%

Section: Density Functional Study On Metal Complexes and Nucleophilicmentioning

confidence: 90%

Section: Synthesismentioning

confidence: 99%

See 1 more Smart Citation

ortho‐Directed Metathetical Fluoride/Amide Exchange in (Pentafluorophenyl)amides

Shutov¹,

Karlov²,

Harms³

et al. 2007

Eur J Inorg Chem

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“…[15c, 18] Product formation is completed by the elimination of cyanide. [19] All SET steps are parto faphotoredox catalytic cycle using visible light as the sole energy source.V ery recently,t he group of Chu independently reported ac omparable transformation exploitingasimilar strategy using trifluoromethyl radicals derived from the To gni II reagent in the presence of 1.5 equiv of Hantzsch ester as ap hotoreductant. [20] Due to the net redox-neutral nature of the sulfonylation/arylation presented here, stoichiometric reagents that do not become part of the product can be avoided.…”

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confidence: 99%

Visible Light-Induced Sulfonylation/Arylation of Styrenes in a Double Radical Three-Component Photoredox Reaction

Lipp¹,

Kammer²,

Kucukdisli³

et al. 2019

Preprint

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Simultaneous sulfonylation/arylation of styrene derivatives is achieved in ap hotoredox-catalyzed threecomponent reaction using visible light. Ab road variety of difunctionalized products is accessible in mostly excellent yields and high diastereoselectivity.T he developed reaction is scalable and suitable for the modification of styrene-functionalized biomolecules. Mechanistic investigations suggest the transformation to be operatingt hrough adesigned sequence of radical formation andradicalcombination.

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Biarylbildung mithilfe von C‐Abgangsgruppen: Warum nicht?

2008

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[3] hierbei wurde allerdings eine Alkyl-und keine Arylgruppe in das Molekül eingeführt. [4] Daher ist es interessant, dass kürzlich eine neue Klasse metallvermittelter Reaktionen beschrieben wurde, die Arylcarbinole, -nitrile und -carbonsäure in guten bis hervorragenden Ausbeuten in Biaryle überführen. Arylnitrile dienen hierbei als elektrophile Komponente in der Kreuzkupplung mit Aryl-Grignard-Reagentien unter Ni-Katalyse, während Arylcarbinole und Arylcarbonsäuren, wie in Schema 2 zusammengefasst, das metallorganische Reagens als Nucleophil in Pd-oder Pd/Cu-vermittelten Reaktionen mit Arylhalogeniden ersetzen.

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Synthesis of azinoazole structural isomers by photocyclization

Cited by 16 publications

References 4 publications

ortho‐Directed Metathetical Fluoride/Amide Exchange in (Pentafluorophenyl)amides

ortho‐Directed Metathetical Fluoride/Amide Exchange in (Pentafluorophenyl)amides

Visible Light-Induced Sulfonylation/Arylation of Styrenes in a Double Radical Three-Component Photoredox Reaction

Biarylbildung mithilfe von C‐Abgangsgruppen: Warum nicht?

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