Abstract
To achieve the goal of green chemistry and sustainable development, catalyst-free reactions and use of naturally abundant resources are gaining importance. In last two decades, C–H functionalization has gained attention for the synthesis of organic molecules. Here, we report a catalyst-free cross-dehydrogenative coupling reaction promoted by visible light for the synthesis of 1,3-oxazines. When α-aminoalkylnaphthols/phenols, commonly known as Betti bases, are irradiated with white light-emitting diode (LED, 23 W) in dimethyl sulfoxide (DMSO) solvent in an open reaction vessel at room temperature, cyclization takes place via α-C–H activation of tertiary amine moiety and forms a new C–O bond. Biologically important 1,3-oxazines are obtained in 58–85% yields. The various advantages of this methodology are (i) the reaction is catalyst-free, (ii) only aerial oxygen is needed as the oxidant, (iii) the reaction is visible light-promoted and (iv) a broad range of 1,3-oxazines are synthesized by varying the tertiary amine moiety or naphthols/phenols or the aryl substituent of the substrate Betti bases.
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Supporting information for characterization of each synthesized compounds are provided including NMR data.
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Abbreviations
- AcOH:
-
Acetic acid
- BHT:
-
Butylated hydroxytoluene
- CDC:
-
Cross-dehydrogenative coupling
- CFL:
-
Compact fluorescent light
- d :
-
Doublet
- DDQ:
-
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
- DMSO:
-
Dimethyl sulfoxide
- DTBP:
-
Di-tert-butyl peroxide
- ESI-HRMS:
-
Electrospray ionization–high-resolution mass spectrometry
- equiv:
-
Equivalent
- FT-IR:
-
Fourier transform infrared
- Hz:
-
Hertz
- IR:
-
Infrared
- J :
-
Coupling constant
- LC/MS:
-
Liquid chromatography/mass spectrometry
- LED:
-
Light-emitting diode
- m :
-
Multiplet
- mg:
-
Milligram
- MHz:
-
Mega Hertz
- mmol:
-
Millimole
- M.P.:
-
Melting point
- MsOH:
-
Methanesulfonic acid
- NIS:
-
N-Iodosuccinimide
- NMR:
-
Nuclear magnetic resonance
- p-TsOH:
-
para-Toluenesulfonic acid
- ppm:
-
Parts per million
- Q-TOF:
-
Quadrupole time-of-flight
- rt:
-
Room temperature
- s :
-
Singlet
- SET:
-
Single-electron transfer
- SI:
-
Supporting Information
- t :
-
Triplet
- TBAI:
-
Tetra-n-butylammonium iodide
- TBHP:
-
tert-Butyl hydroperoxide
- TfOH:
-
Triflic acid
- THIQ:
-
1,2,3,4-Tetrahydroisoquinoline
- TLC:
-
Thin-layer chromatography
- TMS:
-
Tetramethylsilane
- UV:
-
Ultraviolet
- W:
-
Watt
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Acknowledgements
B Shriya Saikia is thankful to the Department of Science & Technology (DST) for the Innovation in Science Pursuit for Inspired Research (INSPIRE) fellowship (Sanction letter No. DST/INSPIRE Fellowship/2019/IF-190236). Mohit L. Deb is thankful to the Science and Engineering Research Board (SERB), India, for the financial support (Grant No. SB/FT/CS-073/2014).
Funding
B Shriya Saikia had received fellowship from the Department of Science & Technology (DST) for carrying out her PhD, and Mohit L. Deb had received funding from the Science and Engineering Research Board (SERB), India.
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MLD and PKB conceptualized the project and BSS performed the experiments. The manuscript is written with the contribution of all the authors.
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Saikia, B.S., Deb, M.L. & Baruah, P.K. Green synthesis of 1,3-oxazines by visible light-promoted catalyst-free C–H activation/cyclization of tertiary amines. Environ Chem Lett 20, 109–118 (2022). https://doi.org/10.1007/s10311-021-01308-6
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DOI: https://doi.org/10.1007/s10311-021-01308-6