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Categories: C-Cl Bond Formation, C-N Bond Formation > Amines

Synthesis of 1,2-chloroamines

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The use of diphenyl selenide as a Lewis base catalyst enables a mild chloroamidation of a wide rand of olefinic substrates including starting materials with acid labile functional groups.
D. W. Tay, I. T. Tsoi, J. C. Er, G. Y. C. Leung, Y.-Y. Yeung, Org. Lett., 2013, 15, 1310-1313.


The use of N3SO2CF3 as an amination reagent and FeCl2 as a chloride source enables an efficient aminochlorination reaction of stryenes . The operationally simple procedure offers mild reaction conditions, good functional group compatibility, and high regioselectivity. Aminobromination using FeBr2 and a one-pot aminoazidation of styrenes are also realized.
J. Zhao, H.-G. Huang, W. Li, W.-B. Liu, Org. Lett., 2021, 23, 5102-5106.


The combination of 2-NsNCl2/2-NsNHNa as the nitrogen and chlorine sources and copper(I) triflate as the catalyst enables a regio- and stereoselective aminochlorination of cinnamic esters to provide anti-alkyl 3-chloro-2-(o-nitrobenzenesulfonamido)-3-phenylpropionate derivatives with good yields and stereoselectivity.
G. Li, H.-X. Wei, S. H. Kim, Org. Lett., 2000, 2, 2249-2252.


A practical, regio- and diastereoselective synthesis of vicinal chloramines from electron-deficient olefins and Chloramine-T is promoted by Brønsted acids in water. This novel protocol is efficient, mild, ecofriendly, and broadly applicable for the aminochlorination of various electron-deficient olefins including α,β-unsaturated ketones, cinnamate, and cinnamide.
X.-L. Wu, G.-W. Wang, J. Org. Chem., 2007, 72, 9398-9401.


The regio- and stereoselective aminochlorination of α,β-unsaturated ketones with N,N-dichloro-p-toluenesulfonamide (4-TsNCl2) and CuOTf as catalyst provides an easy access to vicinal haloamino ketones, with excellent regioselectivity and good yields. Aromatic and aliphatic enones give opposite regioselectivity.
D. Chen, C. Timmons, S. Chao, G. Li, Eur. J. Org. Chem., 2004, 3097-3101.


D. Chen, C. Timmons, S. Chao, G. Li, Eur. J. Org. Chem., 2004, 3097-3101.

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Radical halo-nitration of alkenes proceeds easily by radical addition of nitrogen dioxide generated by thermal decomposition of iron(III) nitrate nonahydrate and subsequent trapping of the resultant radical by a halogen atom in the presence of a halogen salt. Application of this method to synthesis of nitroalkenes is also described.
T. Taniguchi, T. Fuji, H. Ishibashi, J. Org. Chem., 2010, 75, 8126-8132.