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

SCHOOL OF FLEXIBLE ELECTRONICS(FUTURE TECHNOLOGIES)|INSTITUTE OF ADVANCED MATERIALS(IAM)

Nanjing University of Information Science & Technology

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

22 Scopus citations

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.

Original language	English
Pages (from-to)	4070-4074
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.2c01525
State	Published - 10 Jun 2022

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title = "Visible-Light-Promoted Desulfurative Alkylation of Alkyl Thianthrenium Salts with Activated Olefins",

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",

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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

ER -

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

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