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David R. Stuart - One of the best experts on this subject based on the ideXlab platform.

  • Metal‐free Synthesis of Aryl Amines: Beyond Nucleophilic Aromatic Substitution
    Angewandte Chemie (International ed. in English), 2016
    Co-Authors: Alexander H. Sandtorv, David R. Stuart
    Abstract:

    A mild and metal-free approach to C−N coupling is described that employs diaryliodonium salt electrophiles and Secondary Aliphatic Amine nucleophiles. This reaction results in direct ipso-substitution of the iodonium moiety and unsymmetrical aryl(TMP)iodonium salts are primarily employed. Moreover, arene substituents and substitution patterns that currently pose a challenge to classical metal-free methods are accommodated and the alicyclic Amine nucleophiles used here are unprecedented in other contemporary metal-free C−N coupling reactions.

Fátima C. Guedes Da Silva - One of the best experts on this subject based on the ideXlab platform.

  • Addition reactions of primary and Secondary Aliphatic Amines to the benzonitrile ligands in cis- and trans-[PtCl2(NCPh)2] complexes. X-ray structure of the amidine complex trans-[PtCl2{Z-N(H)C(NHBut)Ph}2]
    Inorganica Chimica Acta, 2002
    Co-Authors: Umberto Belluco, Franco Benetollo, Roberta Bertani, Gabriella Bombieri, Rino A. Michelin, Mirto Mozzon, Oliviero Tonon, Armando J. L. Pombeiro, Fátima C. Guedes Da Silva
    Abstract:

    The reactions of cis -[PtCl 2 (NCPh) 2 ] with a fivefold excess of the primary Aliphatic Amines RNH 2 (R=Me, Et, Pr i ) in CH 2 Cl 2 at −10 °C afford in high yield the di-amidine complexes cis -[PtCl 2 {N(H)C(NHR)Ph} 2 ]. The reaction of cis -[PtCl 2 (NCPh) 2 ] with Bu t NH 2 yields the di-amidine complex trans -[PtCl 2 { Z -N(H)C(NHBu t )Ph} 2 ] which has been characterized also by an X-ray diffraction analysis. The corresponding reactions of trans -[PtCl 2 (NCPh) 2 ] with a fivefold excess of RNH 2 (R=Me, Et) afford the di-amidine derivatives trans -[PtCl 2 {N(H)C(NHMe)Ph} 2 ], while the reactions of Pr i NH 2 and Bu t NH 2 lead, for the former, to a mixture of the mono-amidine derivative trans -[PtCl 2 (NCPh){N(H)C(NHPr i )Ph}] and the di-Amine dicationic species derivative trans -[Pt(Pr i NH 2 ) 2 {N(H)C(NHPr i )Ph}[Cl] 2 and, for the latter, to the mono-amidine complex derivative trans -[PtCl 2 (NCPh){N(H)C(NHBu t )Ph}]. The reactions of cis - or trans -[PtCl 2 (NCPh) 2 ] di-nitrile complexes with the Secondary Aliphatic Amine Me 2 NH yields the di-amidine complexes cis - or trans -[PtCl 2 {N(H)C(NMe 2 )Ph} 2 ], while the corresponding reactions with RR′NH (R, R′=Me, Et; R=Me, R′=Bu t ) produce the mono-amidine complexes cis - or trans -[PtCl 2 (NCPh){N(H)C(NRR′ t )Ph}]. The stereochemistry of the amidine ligands in the final products has been investigated by 1 H NMR spectroscopy.

Alexander H. Sandtorv - One of the best experts on this subject based on the ideXlab platform.

  • Metal‐free Synthesis of Aryl Amines: Beyond Nucleophilic Aromatic Substitution
    Angewandte Chemie (International ed. in English), 2016
    Co-Authors: Alexander H. Sandtorv, David R. Stuart
    Abstract:

    A mild and metal-free approach to C−N coupling is described that employs diaryliodonium salt electrophiles and Secondary Aliphatic Amine nucleophiles. This reaction results in direct ipso-substitution of the iodonium moiety and unsymmetrical aryl(TMP)iodonium salts are primarily employed. Moreover, arene substituents and substitution patterns that currently pose a challenge to classical metal-free methods are accommodated and the alicyclic Amine nucleophiles used here are unprecedented in other contemporary metal-free C−N coupling reactions.

Umberto Belluco - One of the best experts on this subject based on the ideXlab platform.

  • Addition reactions of primary and Secondary Aliphatic Amines to the benzonitrile ligands in cis- and trans-[PtCl2(NCPh)2] complexes. X-ray structure of the amidine complex trans-[PtCl2{Z-N(H)C(NHBut)Ph}2]
    Inorganica Chimica Acta, 2002
    Co-Authors: Umberto Belluco, Franco Benetollo, Roberta Bertani, Gabriella Bombieri, Rino A. Michelin, Mirto Mozzon, Oliviero Tonon, Armando J. L. Pombeiro, Fátima C. Guedes Da Silva
    Abstract:

    The reactions of cis -[PtCl 2 (NCPh) 2 ] with a fivefold excess of the primary Aliphatic Amines RNH 2 (R=Me, Et, Pr i ) in CH 2 Cl 2 at −10 °C afford in high yield the di-amidine complexes cis -[PtCl 2 {N(H)C(NHR)Ph} 2 ]. The reaction of cis -[PtCl 2 (NCPh) 2 ] with Bu t NH 2 yields the di-amidine complex trans -[PtCl 2 { Z -N(H)C(NHBu t )Ph} 2 ] which has been characterized also by an X-ray diffraction analysis. The corresponding reactions of trans -[PtCl 2 (NCPh) 2 ] with a fivefold excess of RNH 2 (R=Me, Et) afford the di-amidine derivatives trans -[PtCl 2 {N(H)C(NHMe)Ph} 2 ], while the reactions of Pr i NH 2 and Bu t NH 2 lead, for the former, to a mixture of the mono-amidine derivative trans -[PtCl 2 (NCPh){N(H)C(NHPr i )Ph}] and the di-Amine dicationic species derivative trans -[Pt(Pr i NH 2 ) 2 {N(H)C(NHPr i )Ph}[Cl] 2 and, for the latter, to the mono-amidine complex derivative trans -[PtCl 2 (NCPh){N(H)C(NHBu t )Ph}]. The reactions of cis - or trans -[PtCl 2 (NCPh) 2 ] di-nitrile complexes with the Secondary Aliphatic Amine Me 2 NH yields the di-amidine complexes cis - or trans -[PtCl 2 {N(H)C(NMe 2 )Ph} 2 ], while the corresponding reactions with RR′NH (R, R′=Me, Et; R=Me, R′=Bu t ) produce the mono-amidine complexes cis - or trans -[PtCl 2 (NCPh){N(H)C(NRR′ t )Ph}]. The stereochemistry of the amidine ligands in the final products has been investigated by 1 H NMR spectroscopy.

O. N. Chupakhin - One of the best experts on this subject based on the ideXlab platform.

  • From 3-chloromethyl-1,2,4-triazine 4-oxides to various substituted pyridines and 1,2,4-triazines
    Russian Chemical Bulletin, 2005
    Co-Authors: Valery N. Kozhevnikov, Dmitry N. Kozhevnikov, Olga V. Shabunina, N. N. Kataeva, S. A. Yushchuk, Vladimir L. Rusinov, O. N. Chupakhin
    Abstract:

    An efficient strategy for the synthesis of new pyridine and 1,2,4-triazine derivatives starting from available 6-aryl-3-chloromethyl-1,2,4-triazine 4-oxides was proposed. The deoxygenative nucleophilic hydrogen substitution in the triazine-oxide ring, nucleophilic substitution of the chlorine atom in the side chain, and transformations of the 1,2,4-triazine ring into the pyridine ring via the inverse-electron-demand Diels-Alder reactions, being used in different orders, are a rather flexible tool for the functionalization of the titled heterocycles. The cyanide anion, indoles, thiophenols, Amines, and triphenylphosphine were used as nucleophiles. The direct introduction of indole residues into the 1,2,4-triazine ring followed by the substitution of the chlorine atom by a residue of the primary or Secondary Aliphatic Amine was found to be the most convenient method for the library synthesis.