Ni-catalyzed non-activated C-S bond cleavage at ambient temperature for the synthesis of sulfur-containing polycyclic compounds

Takanori Shibata; Ayato Sekine; Mika Akino; Mamoru Ito

doi:10.1039/d1cc03226g

Ni-catalyzed non-activated C-S bond cleavage at ambient temperature for the synthesis of sulfur-containing polycyclic compounds

Takanori Shibata^*, Ayato Sekine, Mika Akino, Mamoru Ito

^*Corresponding author for this work

School of Advanced Science and Engineering

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

6 Citations (Scopus)

Abstract

A Ni-catalyzed intramolecular reaction of diarylthioether-tethered 1,8-diynes gave sulfur-containing tetracyclic compounds at ambient temperature. The transformation was initiated by non-activated sp²C-S bond cleavage along with consecutive alkyne insertions. A double intramolecular reaction of a tetrayne and an intermolecular reaction of monoynes were also available, and the corresponding polycyclic compounds were obtained. Moreover, the obtained cycloadduct showed photo-catalytic activity in benzylic oxidation.

Original language	English
Pages (from-to)	9048-9051
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	72
DOIs	https://doi.org/10.1039/d1cc03226g
Publication status	Published - 2021 Sept 16

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Access to Document

10.1039/d1cc03226g

Cite this

@article{19a1677997674bcca2d1d73f155c8fc8,

title = "Ni-catalyzed non-activated C-S bond cleavage at ambient temperature for the synthesis of sulfur-containing polycyclic compounds",

abstract = "A Ni-catalyzed intramolecular reaction of diarylthioether-tethered 1,8-diynes gave sulfur-containing tetracyclic compounds at ambient temperature. The transformation was initiated by non-activated sp2C-S bond cleavage along with consecutive alkyne insertions. A double intramolecular reaction of a tetrayne and an intermolecular reaction of monoynes were also available, and the corresponding polycyclic compounds were obtained. Moreover, the obtained cycloadduct showed photo-catalytic activity in benzylic oxidation.",

author = "Takanori Shibata and Ayato Sekine and Mika Akino and Mamoru Ito",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Number 19K05485 and Yamada Science Foundation. We acknowledge Central Glass Co., Ltd for the generous gift of the HFIP. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",

year = "2021",

month = sep,

day = "16",

doi = "10.1039/d1cc03226g",

language = "English",

volume = "57",

pages = "9048--9051",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "72",

}

TY - JOUR

T1 - Ni-catalyzed non-activated C-S bond cleavage at ambient temperature for the synthesis of sulfur-containing polycyclic compounds

AU - Shibata, Takanori

AU - Sekine, Ayato

AU - Akino, Mika

AU - Ito, Mamoru

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Number 19K05485 and Yamada Science Foundation. We acknowledge Central Glass Co., Ltd for the generous gift of the HFIP. Publisher Copyright: © The Royal Society of Chemistry 2021.

PY - 2021/9/16

Y1 - 2021/9/16

N2 - A Ni-catalyzed intramolecular reaction of diarylthioether-tethered 1,8-diynes gave sulfur-containing tetracyclic compounds at ambient temperature. The transformation was initiated by non-activated sp2C-S bond cleavage along with consecutive alkyne insertions. A double intramolecular reaction of a tetrayne and an intermolecular reaction of monoynes were also available, and the corresponding polycyclic compounds were obtained. Moreover, the obtained cycloadduct showed photo-catalytic activity in benzylic oxidation.

AB - A Ni-catalyzed intramolecular reaction of diarylthioether-tethered 1,8-diynes gave sulfur-containing tetracyclic compounds at ambient temperature. The transformation was initiated by non-activated sp2C-S bond cleavage along with consecutive alkyne insertions. A double intramolecular reaction of a tetrayne and an intermolecular reaction of monoynes were also available, and the corresponding polycyclic compounds were obtained. Moreover, the obtained cycloadduct showed photo-catalytic activity in benzylic oxidation.

UR - http://www.scopus.com/inward/record.url?scp=85114674366&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85114674366&partnerID=8YFLogxK

U2 - 10.1039/d1cc03226g

DO - 10.1039/d1cc03226g

M3 - Article

C2 - 34382056

AN - SCOPUS:85114674366

SN - 1359-7345

VL - 57

SP - 9048

EP - 9051

JO - Chemical Communications

JF - Chemical Communications

IS - 72

ER -

Ni-catalyzed non-activated C-S bond cleavage at ambient temperature for the synthesis of sulfur-containing polycyclic compounds

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this