Pd-II- and Pt-II-mediated coupling of aryl isocyanides with N-heterocyclic thiones

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Pd-II- and Pt-II-mediated coupling of aryl isocyanides with N-heterocyclic thiones. / Popov, Roman A.; Mikherdov, Alexander S.; Novikov, Alexander S.; Myznikov, Leonid V.; Boyarskiy, Vadim P.

In: New Journal of Chemistry, Vol. 45, No. 4, 28.01.2021, p. 1785-1789.

Research output: Contribution to journal › Article › peer-review

Author

Popov, Roman A. ; Mikherdov, Alexander S. ; Novikov, Alexander S. ; Myznikov, Leonid V. ; Boyarskiy, Vadim P. / Pd-II- and Pt-II-mediated coupling of aryl isocyanides with N-heterocyclic thiones. In: New Journal of Chemistry. 2021 ; Vol. 45, No. 4. pp. 1785-1789.

BibTeX

@article{3e9ea1e513494c5f8fcd70612c8a079f,

title = "Pd-II- and Pt-II-mediated coupling of aryl isocyanides with N-heterocyclic thiones",

abstract = "The first example of the addition of an ambident nucleophile's endocyclic center to a coordinated isocyanide is reported, namely, the Pd-II- and Pt-II-mediated reaction of aryl isocyanides with N-methylimidazole- and N-methyltriazole-2-thiones resulting in C,S-chelated deprotonated diaminocarbene complexes. The obtained complexes were isolated in good yields (88-95%) and characterized by elemental analysis (C, H, N), high-resolution mass spectrometry, and IR, 1D (H-1, C-13, Pt-195) and 2D (H-1-H-1 COSY, H-1-H-1 NOESY, H-1-C-13 HSQC, H-1-C-13 HMBC) NMR spectroscopies, as well as by single-crystal X-ray diffraction for the four complexes. The favorability of the resulting regioselectivity was confirmed by DFT calculations.",

author = "Popov, {Roman A.} and Mikherdov, {Alexander S.} and Novikov, {Alexander S.} and Myznikov, {Leonid V.} and Boyarskiy, {Vadim P.}",

note = "Funding Information: This work was supported by the Russian Science Foundation (grant 19-13-00008). Physicochemical studies were performed at the Center for Magnetic Resonance, the Center for X-ray Diffraction Studies, and the Center for Chemical Analysis and Materials Research of Saint Petersburg State University. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021.",

year = "2021",

month = jan,

day = "28",

doi = "10.1039/D0NJ05386D",

language = "Английский",

volume = "45",

pages = "1785--1789",

journal = "New Journal of Chemistry",

issn = "1144-0546",

publisher = "Royal Society of Chemistry",

number = "4",

}

RIS

TY - JOUR

T1 - Pd-II- and Pt-II-mediated coupling of aryl isocyanides with N-heterocyclic thiones

AU - Popov, Roman A.

AU - Mikherdov, Alexander S.

AU - Novikov, Alexander S.

AU - Myznikov, Leonid V.

AU - Boyarskiy, Vadim P.

N1 - Funding Information: This work was supported by the Russian Science Foundation (grant 19-13-00008). Physicochemical studies were performed at the Center for Magnetic Resonance, the Center for X-ray Diffraction Studies, and the Center for Chemical Analysis and Materials Research of Saint Petersburg State University. Publisher Copyright: © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021.

PY - 2021/1/28

Y1 - 2021/1/28

N2 - The first example of the addition of an ambident nucleophile's endocyclic center to a coordinated isocyanide is reported, namely, the Pd-II- and Pt-II-mediated reaction of aryl isocyanides with N-methylimidazole- and N-methyltriazole-2-thiones resulting in C,S-chelated deprotonated diaminocarbene complexes. The obtained complexes were isolated in good yields (88-95%) and characterized by elemental analysis (C, H, N), high-resolution mass spectrometry, and IR, 1D (H-1, C-13, Pt-195) and 2D (H-1-H-1 COSY, H-1-H-1 NOESY, H-1-C-13 HSQC, H-1-C-13 HMBC) NMR spectroscopies, as well as by single-crystal X-ray diffraction for the four complexes. The favorability of the resulting regioselectivity was confirmed by DFT calculations.

AB - The first example of the addition of an ambident nucleophile's endocyclic center to a coordinated isocyanide is reported, namely, the Pd-II- and Pt-II-mediated reaction of aryl isocyanides with N-methylimidazole- and N-methyltriazole-2-thiones resulting in C,S-chelated deprotonated diaminocarbene complexes. The obtained complexes were isolated in good yields (88-95%) and characterized by elemental analysis (C, H, N), high-resolution mass spectrometry, and IR, 1D (H-1, C-13, Pt-195) and 2D (H-1-H-1 COSY, H-1-H-1 NOESY, H-1-C-13 HSQC, H-1-C-13 HMBC) NMR spectroscopies, as well as by single-crystal X-ray diffraction for the four complexes. The favorability of the resulting regioselectivity was confirmed by DFT calculations.

UR - http://www.scopus.com/inward/record.url?scp=85100378505&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/a009cb50-cc96-3722-a4db-7c836c9e6aa9/

U2 - 10.1039/D0NJ05386D

DO - 10.1039/D0NJ05386D

M3 - статья

VL - 45

SP - 1785

EP - 1789

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

IS - 4

ER -

ID: 71719939