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Synthesis of benzyl azides

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Azide transfer of 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP) to alcohols proceeds to give the corresponding azides under mild reaction conditions. The organic azides were easily isolated because the byproducts are highly soluble in water.
M. Kitamura, T. Koga, M. Yano, T. Okauchi, Synlett, 2012, 23, 1335-1338.


A practical, rapid, and efficient microwave (MW) promoted nucleophilic substitution of alkyl halides or tosylates with alkali azides, thiocyanates or sulfinates in aqueous media tolerates various reactive functional groups.
Y. Ju, D. Kumar, R. S. Varma, J. Org. Chem., 2006, 71, 6697-6700.


The use of copper-catalyzed visible light photochemistry and the Zhdankin azidoiodinane reagent enables an azidation method for C-N bond formation at benzylic C-H positions via a radical chain reaction. The method is applicable to a wide range of substrates bearing different functional groups and having a primary, secondary, or tertiary benzylic position.
P. T. G. Rabet, G. Fumagalli, S. Boyd, M. F. Greaney, Org. Lett., 2016, 18, 1645-1649.


A bismuth(III)-catalyzed direct azidation of sec-benzyl alcohols provided sec-benzyl azides in good yield within a short reaction time.
J. Tummatorn, C. Thongsornkleeb, S. Ruchirawat, P. Thongaram, B. Kaewmee, Synthesis, 2015, 47, 323-329.


The use of azidotrimethylsilane (TMSN3) as azide source in the presence of copper(II) triflate [Cu(OTf)2] enables a simple, practical, and efficient direct synthesis of organic azides in good yields from secondary benzylic alcohols.
P. Khedar, K. Pericherla, A. Kumar, Synlett, 2014, 25, 515-518.


The sensitive azidocarbenium ion intermediate can be trapped with various nucleophiles to provide azides in excellent chemoselectivity. The method enables the chemoselective synthesis of primary and secondary benzyl azides from aldehydes in a one-pot reaction.
S. Pramanik, P. Ghorai, Org. Lett., 2014, 16, 2104-2107.


A catalytic amount of iron trichloride enables as C-C and C-N bond formation reactions of O-heterocycles accompanied by ring opening in the presence of TMSN3 or allylsilanes. The reactions smoothly proceeded at room temperature to give the corresponding primary saturated alcohols from 2-substituted tetrahydrofurans, ortho-substituted benzyl alcohols from phthalanes, and saturated carboxylic acids from lactones in high yields.
Y. Sawama, K. Shibata, Y. Sawama, M. Takubo, Y. Monguchi, N. Krause, H. Sajiki, Org. Lett., 2013, 15, 5282-5285.


A photoredox-catalyzed azidotrifluoromethylation of substituted styrenes as well as various activated and nonactivated alkenes using [Ru(bpy)3(PF6)2] as the photocatalyst and Umemoto’s reagent as the CF3 source delivers a wide range β-trifluoromethylated azides or amines in good yields.
G. Dagousset, A. Carboni, E. Magnier, G. Masson, Org. Lett., 2014, 16, 4340-4343.