10.1002/anie.201705025
Angewandte Chemie International Edition
COMMUNICATION
chromatography using silica gel as stationary phase and mixtures of
pentane/diethyl ether as eluent.
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[9]
NH-Dibenzothiophenesulfoximine 4 can easily be prepared from the
corresponding sulfoxide (for details, see Supporting Information). N-
Arylated derivatives 1 have then been obtained following standard
protocols described in: a) C. Bolm, J. P. Hildebrand, Tetrahedron Lett.
1998, 39, 5731-5734; b) C. Bolm, J. P. Hildebrand, J. Org. Chem. 2000,
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911-913; d) G. Y. Cho, P. Remy, J. Jansson, C. Moessner, C. Bolm,
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General procedure for the reaction of amides 5 with dibenzothiophene
sulfoximine 4 (Scheme 4): Amide 5 (0.2 mmol), sulfoximine 4 (86.1 mg,
0.4 mmol, 2 equiv), Cu(OAc)2 (7.3 mg, 0.04 mmol, 20 mol %) and
pyridine (0.4 mL) were combined in a 10 mL sealed tube, and the
reaction mixture was stirred at 100 °C. After consumption of the amide
(commonly after 10-48 h, as revealed by TLC), TTMSS (149.2 mg, 0.6
mmol, 3.0 equiv) and AIBN (13.1 mg, 0.08 mmol, 40 mol %) were
sequentially added. Stirring was continued at 100 °C for 2-4 d, and after
consumption of the starting material (commonly after 2-4 d, as revealed
by TLC), the mixture was cooled to room temperature. Aminated product
6 was isolated and purified by column chromatography using silica gel as
stationary phase and mixtures of pentane/ethyl acetate as eluent.
[10] N-Substituted dibenzothiophene sulfilimines have been used for the
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Acknowledgements
H.Y. thanks the China Scholarship Council for pre-doctoral
stipend.
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Keywords: amination • primary amines • radical cleavage • NH3
surrogate • dibenzothiophene sulfoximine
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