TY - JOUR

T1 - Synthesis and structure of (Nitronyl nitroxide-2-ido)(tert-butyldiphenylphosphine)gold(i) and-(di(tert-butyl)phenylphosphine)gold(i) derivatives; their comparative study in the cross-coupling reaction

AU - Zayakin, Igor

AU - Bagryanskaya, Irina

AU - Stass, Dmitri

AU - Kazantsev, Maxim

AU - Tretyakov, Evgeny

N1 - Publisher Copyright: © 2020 by the authors. Licensee MDPI, Basel, Switzerland.

PY - 2020/9

Y1 - 2020/9

N2 - We synthesized two new organogold derivatives of a nitronyl nitroxide (NN) with phosphine ligands, namely NN-Au-PtBuPh2 and NN-Au-PtBu2Ph. They were characterized by X-ray diffraction analysis, cyclic voltammetry, and ESR, IR, and UV/Vis spectroscopy. The X-ray structural analysis revealed a tendency of the NN moiety to form a large number of short intermolecular contacts. This phenomenon is related to the anionic nature of the paramagnetic group NN, as evidenced by a significantly lower oxidation potential in comparison with purely organic derivatives of NN radicals. The cross-coupling reaction of NN-Au-PPh3, NN-Au-PtBuPh2, or NN-Au-PtBu2Ph with an activated bromoarene, namely, p-BrC6H4NO2, was investigated. It was shown that regardless of the presence of the bulky tert-butyl substituent, all gold derivatives have similar activities in the cross-coupling reaction and give a cross-coupling product, NN-C6H4NO2, with comparable yields.

AB - We synthesized two new organogold derivatives of a nitronyl nitroxide (NN) with phosphine ligands, namely NN-Au-PtBuPh2 and NN-Au-PtBu2Ph. They were characterized by X-ray diffraction analysis, cyclic voltammetry, and ESR, IR, and UV/Vis spectroscopy. The X-ray structural analysis revealed a tendency of the NN moiety to form a large number of short intermolecular contacts. This phenomenon is related to the anionic nature of the paramagnetic group NN, as evidenced by a significantly lower oxidation potential in comparison with purely organic derivatives of NN radicals. The cross-coupling reaction of NN-Au-PPh3, NN-Au-PtBuPh2, or NN-Au-PtBu2Ph with an activated bromoarene, namely, p-BrC6H4NO2, was investigated. It was shown that regardless of the presence of the bulky tert-butyl substituent, all gold derivatives have similar activities in the cross-coupling reaction and give a cross-coupling product, NN-C6H4NO2, with comparable yields.

KW - ESR spectroscopy

KW - Nitronyl nitroxide

KW - Organogold derivatives

KW - Pd(0)-catalyzed cross-coupling

KW - X-ray diffraction analysis

KW - nitronyl nitroxide

KW - NITRONYL

KW - RADICALS

KW - organogold derivatives

UR - http://www.scopus.com/inward/record.url?scp=85090524267&partnerID=8YFLogxK

U2 - 10.3390/cryst10090770

DO - 10.3390/cryst10090770

M3 - Article

AN - SCOPUS:85090524267

VL - 10

SP - 1

EP - 12

JO - Crystals

JF - Crystals

SN - 2073-4352

IS - 9

M1 - 770

ER -