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Synlett 2024; 35(03): 291-296
DOI: 10.1055/a-2131-3208
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Organic Chemistry Under Visible Light: Photolytic and Photocatalytic Organic Transformations

Visible-Light-Driven Denitrogenative C–C Bond Formation and Oxidative Difunctionalization of Vinyl Azides

Santosh Sing Sardar
a   Department of Chemistry, Visva-Bharati (A Central University), Santiniketan-731235, India
,
Aramita De
a   Department of Chemistry, Visva-Bharati (A Central University), Santiniketan-731235, India
,
Satyajit Pal
a   Department of Chemistry, Visva-Bharati (A Central University), Santiniketan-731235, India
,
Subhankar Sarkar
a   Department of Chemistry, Visva-Bharati (A Central University), Santiniketan-731235, India
,
Sougata Santra 
b   Department of Organic & Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, 19 Mira Str., Yekaterinburg, 620002, Russian Federation
,
Grigory V. Zyryanov
b   Department of Organic & Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, 19 Mira Str., Yekaterinburg, 620002, Russian Federation
c   I. Ya. Postovskiy Institute of Organic Synthesis, Ural Division of the Russian Academy of Sciences, 22 S. Kovalevskoy Str., Yekaterinburg, 620219, Russian Federation
,
Adinath Majee∗
a   Department of Chemistry, Visva-Bharati (A Central University), Santiniketan-731235, India
› Author AffiliationsA. Majee acknowledges financial support from the Council of Scientific and Industrial Research, India (CSIR) Major Research Project (Ref. No. 02(0383)/19/EMR-II). S. Sing Sardar acknowledges CSIR for his fellowship (Award No. 09/202(0116)/2020-EMR-I). We are thankful to the Department of Science and Technology, Ministry of Science and Technology, India (DST) FIST program and the University Grants Commission (UGC) SAP program of the Department of Chemistry, Visva-Bharati.
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Abstract

A newer synthetic protocol has been developed to synthesize α-oxyalkyl ketones from vinyl azides under transition-metal-free reaction conditions. The reaction proceeds in the presence of organic photoredox catalyst rose bengal, an oxidant tert-butyl hydroperoxide (TBHP), and ethers. A broad range of substituted vinyl azides were found to react smoothly upon visible-light irradiation, which readily furnished the related products. Several control experiments have been done to suggest a probable mechanism. The process is initiated by radical addition to vinyl azide, which triggers a cascade fragmentation mechanism driven by the loss of dinitrogen and the stabilized ether radical ultimately produces the α-oxyalkyl ketones. This method provides a simple, mild, straight forward, novel paradigm to prepare α-oxyalkyl ketones.

Key words

visible light - rose bengal - α-oxyalkyl ketones - oxidative difunctionalization - vinyl azides

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2131-3208.
  • Supporting Information


Publication History

Received: 23 May 2023

Accepted after revision: 17 July 2023

Accepted Manuscript online:
17 July 2023

Article published online:
12 September 2023

© 2023. Thieme. All rights reserved

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  • 60 General Procedure for the Synthesis of α-Oxyalkyl Ketones (3 and 5) TBHP (3.00 equiv., 5–6 M in decane) and rose bengal (2 mol%) were added to a mixture of vinyl azides (1, 0.5mmol) and ethers. After that, this mixture was stirred at room temperature in 1,2-DCE for 24 h in the presence of blue LED, where ether and 1,2-DCE were used a 1:1 volume ratio (2 mL). After completion of the reaction (TLC), the mixture was diluted with saturated saline water (2 times) and extracted with DCM. The combined organic layers were collected and dried over anhydrous Na2SO4. The residue was purified by column chromatography on silica gel to afford the desired products (3, 5; eluent: PE/ethyl acetate). General Procedure for the Synthesis of 1-Substituted Vinyl Azide (1) The synthesis of 1 was carried out according to the previously described method.23,27 In a round-bottom flask, 10 mmol of styrene (1.041 g) was taken into CH2Cl2 (8 mL) and stirred at room temperature. Bromine (1.600 g, 10 mmol) in CH2Cl2 (6 mL) was added slowly and stirred for 2 h. Then, the CH2Cl2 was removed in a vacuum to get the 1-(1,2- dibromoethyl)benzene residue as a crystalline solid (2.481 g, 94%). 1-(1,2- Dibromoethyl)benzene (2.481 g, 9.4 mmol) was dissolved in 14 mL of dimethyl sulfoxide. After a slow stream of N2 was passed through the apparatus, sodium azide (0.975 g, 15 mmol) was slowly added to the solution for 45 min afterward. The mixture became thick with precipitated azido bromide and was stirred for a further 13 h at room temperature. After treatment with 0.4 g (10 mmol) of sodium hydroxide in 0.4 mL of deionized water, the reaction mixture was stirred at room temperature for 24 h. Then, the mixture was poured into 40 mL of 2% sodium bicarbonate aqueous solution and extracted with dichloromethane. The extract was washed with deionized water. Dichloromethane was removed in a vacuum and evaporated to yield crude 1-azidostyrene as a red oil. The oil was passed through a silica gel column using petroleum ether as eluent. The eluent was removed in a vacuum, and the corresponding vinyl azide was obtained. Precautions for Safe Handling of Azides, TBHP, and Bromine All of those chemicals were used under the fuming hood. Chemicals were kept away from open flames, hot surfaces, and ignition sources. If any of the chemicals contact with a body part, wash that body part as soon as possible.