Visible-Light-Promoted Desulfurative Alkylation of Alkyl Thianthrenium Salts with Activated Olefins

Xin Li; Weili Si; Zhanhui Liu; Haitao Qian; Tingxue Wang; Shengnan Leng; Jinwei Sun; Yan Jiao; Xuan Zhang

doi:10.1021/acs.orglett.2c01525

Visible-Light-Promoted Desulfurative Alkylation of Alkyl Thianthrenium Salts with Activated Olefins

Xin Li, Weili Si, Zhanhui Liu, Haitao Qian, Tingxue Wang, Shengnan Leng, Jinwei Sun, Yan Jiao, Xuan Zhang

柔性电子（未来科技）学院|先进材料研究院

Nanjing University of Information Science & Technology

科研成果: 期刊稿件 › 文章 › 同行评审

22 引用（Scopus）

摘要

Reactions involving an alkyl radical generated from a primary alcohol by photochemistry are rare and challenging. Herein, we present a photocatalyst- and metal-free approach that enables the generation of an alkyl radical from the corresponding alcohol and the subsequent C(sp3)-C(sp3) bond formation with activated olefin, via an alkyl thianthrenium salt/Hantzsch ester electron donor-acceptor complex. This protocol for the conversion of a C-OH bond to a C-C bond is highly functionality tolerant and can successfully be used in late-stage functionalization of pharmaceuticals.

源语言	英语
页（从-至）	4070-4074
页数	5
期刊	Organic Letters
卷	24
期	22
DOI	https://doi.org/10.1021/acs.orglett.2c01525
出版状态	已出版 - 10 6月 2022

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abstract = "Reactions involving an alkyl radical generated from a primary alcohol by photochemistry are rare and challenging. Herein, we present a photocatalyst- and metal-free approach that enables the generation of an alkyl radical from the corresponding alcohol and the subsequent C(sp3)-C(sp3) bond formation with activated olefin, via an alkyl thianthrenium salt/Hantzsch ester electron donor-acceptor complex. This protocol for the conversion of a C-OH bond to a C-C bond is highly functionality tolerant and can successfully be used in late-stage functionalization of pharmaceuticals.",

author = "Xin Li and Weili Si and Zhanhui Liu and Haitao Qian and Tingxue Wang and Shengnan Leng and Jinwei Sun and Yan Jiao and Xuan Zhang",

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doi = "10.1021/acs.orglett.2c01525",

language = "英语",

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T1 - Visible-Light-Promoted Desulfurative Alkylation of Alkyl Thianthrenium Salts with Activated Olefins

AU - Li, Xin

AU - Si, Weili

AU - Liu, Zhanhui

AU - Qian, Haitao

AU - Wang, Tingxue

AU - Leng, Shengnan

AU - Sun, Jinwei

AU - Jiao, Yan

AU - Zhang, Xuan

PY - 2022/6/10

Y1 - 2022/6/10

N2 - Reactions involving an alkyl radical generated from a primary alcohol by photochemistry are rare and challenging. Herein, we present a photocatalyst- and metal-free approach that enables the generation of an alkyl radical from the corresponding alcohol and the subsequent C(sp3)-C(sp3) bond formation with activated olefin, via an alkyl thianthrenium salt/Hantzsch ester electron donor-acceptor complex. This protocol for the conversion of a C-OH bond to a C-C bond is highly functionality tolerant and can successfully be used in late-stage functionalization of pharmaceuticals.

AB - Reactions involving an alkyl radical generated from a primary alcohol by photochemistry are rare and challenging. Herein, we present a photocatalyst- and metal-free approach that enables the generation of an alkyl radical from the corresponding alcohol and the subsequent C(sp3)-C(sp3) bond formation with activated olefin, via an alkyl thianthrenium salt/Hantzsch ester electron donor-acceptor complex. This protocol for the conversion of a C-OH bond to a C-C bond is highly functionality tolerant and can successfully be used in late-stage functionalization of pharmaceuticals.

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U2 - 10.1021/acs.orglett.2c01525

DO - 10.1021/acs.orglett.2c01525

M3 - 文章

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AN - SCOPUS:85131772146

SN - 1523-7060

VL - 24

SP - 4070

EP - 4074

JO - Organic Letters

JF - Organic Letters

IS - 22

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Visible-Light-Promoted Desulfurative Alkylation of Alkyl Thianthrenium Salts with Activated Olefins

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