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.
Related
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.