Tin(II)-Nitrene Radical Complexes Formed by Electron Transfer from Redox-Active Ligand to Organic Azides and Their Reactivity in C(sp3)-H Activation

Hideki Sugimoto; Mayuka Yano; Kazunobu Sato; Mayuko Miyanishi; Kenji Sugisaki; Yoshihito Shiota; Akira Kaga; Kazunari Yoshizawa; Shinobu Itoh

doi:10.1021/acs.inorgchem.1c02806

Tin(II)-Nitrene Radical Complexes Formed by Electron Transfer from Redox-Active Ligand to Organic Azides and Their Reactivity in C(sp³)-H Activation

Hideki Sugimoto, Mayuka Yano, Kazunobu Sato, Mayuko Miyanishi, Kenji Sugisaki, Yoshihito Shiota, Akira Kaga, Kazunari Yoshizawa, Shinobu Itoh

Department of Fundamental Organic Chemistry

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

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Abstract

A tin(II) complex coordinated by a sterically demanding o-phenylenediamido ligand is synthesized. The ligand is redox-active to reach a tin(II) complex with the diiminobenzosemiquinone radial anion in the oxidation by AgPF6. The tin(II) complex reacts with a series of nosylazides (x-NO2C6H4-SO2-N3; x = o, m, or p) at -30 °C to yield the corresponding nitrene radical bound tin(II) complexes. The nitrene radical complexes exhibit C(sp3)-H activation and amination reactivity.

Original language	English
Journal	Inorganic chemistry
DOIs	https://doi.org/10.1021/acs.inorgchem.1c02806
Publication status	Accepted/In press - 2021

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Inorganic Chemistry

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10.1021/acs.inorgchem.1c02806

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@article{a2c0605a48c4419bb2815e1a8b02346a,

title = "Tin(II)-Nitrene Radical Complexes Formed by Electron Transfer from Redox-Active Ligand to Organic Azides and Their Reactivity in C(sp3)-H Activation",

abstract = "A tin(II) complex coordinated by a sterically demanding o-phenylenediamido ligand is synthesized. The ligand is redox-active to reach a tin(II) complex with the diiminobenzosemiquinone radial anion in the oxidation by AgPF6. The tin(II) complex reacts with a series of nosylazides (x-NO2C6H4-SO2-N3; x = o, m, or p) at -30 °C to yield the corresponding nitrene radical bound tin(II) complexes. The nitrene radical complexes exhibit C(sp3)-H activation and amination reactivity.",

author = "Hideki Sugimoto and Mayuka Yano and Kazunobu Sato and Mayuko Miyanishi and Kenji Sugisaki and Yoshihito Shiota and Akira Kaga and Kazunari Yoshizawa and Shinobu Itoh",

note = "Funding Information: This work was supported by KAKENHI (Grant-in-Aid) for Scientific Research (No. 19K05497) and by JST-CREST (JPMJCR16P1). Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

doi = "10.1021/acs.inorgchem.1c02806",

language = "English",

journal = "Inorganic Chemistry",

issn = "0020-1669",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - Tin(II)-Nitrene Radical Complexes Formed by Electron Transfer from Redox-Active Ligand to Organic Azides and Their Reactivity in C(sp3)-H Activation

AU - Sugimoto, Hideki

AU - Yano, Mayuka

AU - Sato, Kazunobu

AU - Miyanishi, Mayuko

AU - Sugisaki, Kenji

AU - Shiota, Yoshihito

AU - Kaga, Akira

AU - Yoshizawa, Kazunari

AU - Itoh, Shinobu

PY - 2021

Y1 - 2021

N2 - A tin(II) complex coordinated by a sterically demanding o-phenylenediamido ligand is synthesized. The ligand is redox-active to reach a tin(II) complex with the diiminobenzosemiquinone radial anion in the oxidation by AgPF6. The tin(II) complex reacts with a series of nosylazides (x-NO2C6H4-SO2-N3; x = o, m, or p) at -30 °C to yield the corresponding nitrene radical bound tin(II) complexes. The nitrene radical complexes exhibit C(sp3)-H activation and amination reactivity.

AB - A tin(II) complex coordinated by a sterically demanding o-phenylenediamido ligand is synthesized. The ligand is redox-active to reach a tin(II) complex with the diiminobenzosemiquinone radial anion in the oxidation by AgPF6. The tin(II) complex reacts with a series of nosylazides (x-NO2C6H4-SO2-N3; x = o, m, or p) at -30 °C to yield the corresponding nitrene radical bound tin(II) complexes. The nitrene radical complexes exhibit C(sp3)-H activation and amination reactivity.

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U2 - 10.1021/acs.inorgchem.1c02806

DO - 10.1021/acs.inorgchem.1c02806

M3 - Article

C2 - 34779619

AN - SCOPUS:85119980487

SN - 0020-1669

JO - Inorganic Chemistry

JF - Inorganic Chemistry

ER -

Tin(II)-Nitrene Radical Complexes Formed by Electron Transfer from Redox-Active Ligand to Organic Azides and Their Reactivity in C(sp³)-H Activation

Abstract

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