Photocatalytic α-Acylation of Ethers

Zhongdong Sun; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1021/acs.orglett.7b01552

Photocatalytic α-Acylation of Ethers

Zhongdong Sun, Naoya Kumagai, Masakatsu Shibasaki

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

50 Citations (Scopus)

Abstract

Direct coupling of ethers and acyl halides was promoted by a binary catalytic system comprising an Ir-based photocatalyst and a Ni complex under blue-light irradiation. Photocatalysts with high triplet energy directed the catalysis, and the reaction likely proceeded by triplet-triplet energy transfer from the excited photocatalysts. Chlorine radicals generated from an excited Ni complex bearing a Ni-Cl bond would be responsible for generating α-oxy radicals leading to the α-acylated ethers.

Original language	English
Pages (from-to)	3727-3730
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.7b01552
Publication status	Published - 2017 Jul 21
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Photocatalytic α-Acylation of Ethers",

abstract = "Direct coupling of ethers and acyl halides was promoted by a binary catalytic system comprising an Ir-based photocatalyst and a Ni complex under blue-light irradiation. Photocatalysts with high triplet energy directed the catalysis, and the reaction likely proceeded by triplet-triplet energy transfer from the excited photocatalysts. Chlorine radicals generated from an excited Ni complex bearing a Ni-Cl bond would be responsible for generating α-oxy radicals leading to the α-acylated ethers.",

author = "Zhongdong Sun and Naoya Kumagai and Masakatsu Shibasaki",

note = "Funding Information: This work was financially supported by ACT-C (JPMJCR12YO) from JST and KAKENHI (25713002, 17H03025, and JP16H01043 in Precisely Designed Catalysts with Customized Scaffolding) from JSPS. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b01552",

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T1 - Photocatalytic α-Acylation of Ethers

AU - Sun, Zhongdong

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

N1 - Funding Information: This work was financially supported by ACT-C (JPMJCR12YO) from JST and KAKENHI (25713002, 17H03025, and JP16H01043 in Precisely Designed Catalysts with Customized Scaffolding) from JSPS. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/7/21

Y1 - 2017/7/21

N2 - Direct coupling of ethers and acyl halides was promoted by a binary catalytic system comprising an Ir-based photocatalyst and a Ni complex under blue-light irradiation. Photocatalysts with high triplet energy directed the catalysis, and the reaction likely proceeded by triplet-triplet energy transfer from the excited photocatalysts. Chlorine radicals generated from an excited Ni complex bearing a Ni-Cl bond would be responsible for generating α-oxy radicals leading to the α-acylated ethers.

AB - Direct coupling of ethers and acyl halides was promoted by a binary catalytic system comprising an Ir-based photocatalyst and a Ni complex under blue-light irradiation. Photocatalysts with high triplet energy directed the catalysis, and the reaction likely proceeded by triplet-triplet energy transfer from the excited photocatalysts. Chlorine radicals generated from an excited Ni complex bearing a Ni-Cl bond would be responsible for generating α-oxy radicals leading to the α-acylated ethers.

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Photocatalytic α-Acylation of Ethers

Abstract

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