Red-light-mediated BartonMcCombie reaction

Akihiro Ogura; Naoki Ichii; Kouhei Shibata; Ken Ichi Takao

doi:10.1246/BCSJ.20200087

Red-light-mediated BartonMcCombie reaction

Akihiro Ogura, Naoki Ichii, Kouhei Shibata, Ken Ichi Takao

Department of Applied Chemistry

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

1 Citation (Scopus)

Abstract

A red-light-mediated BartonMcCombie reaction is described, in which chlorophyll a is used as a photocatalyst and tris(trimethylsilyl)silane or Hantzsch ester is used as the hydrogen source. The reaction can be performed with a set of easily available equipment and reagents, and a variety of linear and cyclic xanthates could be applied. In contrast to the traditional conditions, the reaction does not involve toxic organotin or an explosive radical initiator. The reaction mechanism was analyzed both by experiments and computation, and it was suggested that the radical chain mechanism initiated by excitation of complex followed by charge transfer is likely to be operative.

Original language	English
Pages (from-to)	936-941
Number of pages	6
Journal	Bulletin of the Chemical Society of Japan
Volume	93
Issue number	7
DOIs	https://doi.org/10.1246/BCSJ.20200087
Publication status	Published - 2020 Jul

Keywords

Barton–McCombie reaction
Chlorophyll a
Red light

ASJC Scopus subject areas

Chemistry(all)

Access to Document

10.1246/BCSJ.20200087

Cite this

@article{65fa5fdc0bae45cab6b38c63008c9514,

title = "Red-light-mediated BartonMcCombie reaction",

abstract = "A red-light-mediated BartonMcCombie reaction is described, in which chlorophyll a is used as a photocatalyst and tris(trimethylsilyl)silane or Hantzsch ester is used as the hydrogen source. The reaction can be performed with a set of easily available equipment and reagents, and a variety of linear and cyclic xanthates could be applied. In contrast to the traditional conditions, the reaction does not involve toxic organotin or an explosive radical initiator. The reaction mechanism was analyzed both by experiments and computation, and it was suggested that the radical chain mechanism initiated by excitation of complex followed by charge transfer is likely to be operative.",

keywords = "Barton–McCombie reaction, Chlorophyll a, Red light",

author = "Akihiro Ogura and Naoki Ichii and Kouhei Shibata and Takao, {Ken Ichi}",

note = "Funding Information: The authors are grateful to the Tobe Maki Scholarship Foundation, Keio Gijuku Academic Development Funds, and Keio Leading-edge Laboratory of Science and Technology for financial support. We acknowledge Prof. Yasushi Katayama and Dr. Nobuyuki Serizawa at Keio University for electrochemical measurements. We also acknowledge Prof. Shunsuke Chiba at Nanyang Technological University for helpful discus- Publisher Copyright: {\textcopyright} 2020 Chemical Society of Japan. All rights reserved.",

year = "2020",

month = jul,

doi = "10.1246/BCSJ.20200087",

language = "English",

volume = "93",

pages = "936--941",

journal = "Bulletin of the Chemical Society of Japan",

issn = "0009-2673",

publisher = "Chemical Society of Japan",

number = "7",

}

TY - JOUR

T1 - Red-light-mediated BartonMcCombie reaction

AU - Ogura, Akihiro

AU - Ichii, Naoki

AU - Shibata, Kouhei

AU - Takao, Ken Ichi

N1 - Funding Information: The authors are grateful to the Tobe Maki Scholarship Foundation, Keio Gijuku Academic Development Funds, and Keio Leading-edge Laboratory of Science and Technology for financial support. We acknowledge Prof. Yasushi Katayama and Dr. Nobuyuki Serizawa at Keio University for electrochemical measurements. We also acknowledge Prof. Shunsuke Chiba at Nanyang Technological University for helpful discus- Publisher Copyright: © 2020 Chemical Society of Japan. All rights reserved.

PY - 2020/7

Y1 - 2020/7

N2 - A red-light-mediated BartonMcCombie reaction is described, in which chlorophyll a is used as a photocatalyst and tris(trimethylsilyl)silane or Hantzsch ester is used as the hydrogen source. The reaction can be performed with a set of easily available equipment and reagents, and a variety of linear and cyclic xanthates could be applied. In contrast to the traditional conditions, the reaction does not involve toxic organotin or an explosive radical initiator. The reaction mechanism was analyzed both by experiments and computation, and it was suggested that the radical chain mechanism initiated by excitation of complex followed by charge transfer is likely to be operative.

AB - A red-light-mediated BartonMcCombie reaction is described, in which chlorophyll a is used as a photocatalyst and tris(trimethylsilyl)silane or Hantzsch ester is used as the hydrogen source. The reaction can be performed with a set of easily available equipment and reagents, and a variety of linear and cyclic xanthates could be applied. In contrast to the traditional conditions, the reaction does not involve toxic organotin or an explosive radical initiator. The reaction mechanism was analyzed both by experiments and computation, and it was suggested that the radical chain mechanism initiated by excitation of complex followed by charge transfer is likely to be operative.

KW - Barton–McCombie reaction

KW - Chlorophyll a

KW - Red light

UR - http://www.scopus.com/inward/record.url?scp=85095110243&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85095110243&partnerID=8YFLogxK

U2 - 10.1246/BCSJ.20200087

DO - 10.1246/BCSJ.20200087

M3 - Article

AN - SCOPUS:85095110243

SN - 0009-2673

VL - 93

SP - 936

EP - 941

JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

IS - 7

ER -

Red-light-mediated BartonMcCombie reaction

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this