Photocatalytic Redox-Neutral Alkoxyacylation of Alkenes

Fu Tong Cen; Yu Sun; Jian Ping Qu; Yan Biao Kang

doi:10.1021/acs.orglett.3c03583

Photocatalytic Redox-Neutral Alkoxyacylation of Alkenes

Fu Tong Cen, Yu Sun, Jian Ping Qu, Yan Biao Kang

School of Chemistry and Moleculai Engineering

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

3 Scopus citations

Abstract

β-Alkoxyketones are important building blocks in organic synthesis. By utilizing CBZ6, with an oxidative potential of −2.16 V (vs the saturated calomel electrode), as a redox-neutral photocatalyst, alkoxyacylation of olefins was accomplished under the irradiation of visible light via a cationic intermediate. It involves the addition of an acyl radical to olefin to form a radical intermediate and the following oxidation of the radical intermediate to the benzyl cationic intermediate that is captured by alkoxy anions. This process provides concise and practical access to the β-functionalized ketones.

Original language	English
Pages (from-to)	8997-9001
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	50
DOIs	https://doi.org/10.1021/acs.orglett.3c03583
State	Published - 22 Dec 2023

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abstract = "β-Alkoxyketones are important building blocks in organic synthesis. By utilizing CBZ6, with an oxidative potential of −2.16 V (vs the saturated calomel electrode), as a redox-neutral photocatalyst, alkoxyacylation of olefins was accomplished under the irradiation of visible light via a cationic intermediate. It involves the addition of an acyl radical to olefin to form a radical intermediate and the following oxidation of the radical intermediate to the benzyl cationic intermediate that is captured by alkoxy anions. This process provides concise and practical access to the β-functionalized ketones.",

author = "Cen, {Fu Tong} and Yu Sun and Qu, {Jian Ping} and Kang, {Yan Biao}",

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T1 - Photocatalytic Redox-Neutral Alkoxyacylation of Alkenes

AU - Cen, Fu Tong

AU - Sun, Yu

AU - Qu, Jian Ping

AU - Kang, Yan Biao

PY - 2023/12/22

Y1 - 2023/12/22

N2 - β-Alkoxyketones are important building blocks in organic synthesis. By utilizing CBZ6, with an oxidative potential of −2.16 V (vs the saturated calomel electrode), as a redox-neutral photocatalyst, alkoxyacylation of olefins was accomplished under the irradiation of visible light via a cationic intermediate. It involves the addition of an acyl radical to olefin to form a radical intermediate and the following oxidation of the radical intermediate to the benzyl cationic intermediate that is captured by alkoxy anions. This process provides concise and practical access to the β-functionalized ketones.

AB - β-Alkoxyketones are important building blocks in organic synthesis. By utilizing CBZ6, with an oxidative potential of −2.16 V (vs the saturated calomel electrode), as a redox-neutral photocatalyst, alkoxyacylation of olefins was accomplished under the irradiation of visible light via a cationic intermediate. It involves the addition of an acyl radical to olefin to form a radical intermediate and the following oxidation of the radical intermediate to the benzyl cationic intermediate that is captured by alkoxy anions. This process provides concise and practical access to the β-functionalized ketones.

UR - http://www.scopus.com/inward/record.url?scp=85180098226&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.3c03583

DO - 10.1021/acs.orglett.3c03583

M3 - 文章

C2 - 38060991

AN - SCOPUS:85180098226

SN - 1523-7060

VL - 25

SP - 8997

EP - 9001

JO - Organic Letters

JF - Organic Letters

IS - 50

ER -

Photocatalytic Redox-Neutral Alkoxyacylation of Alkenes

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