Categories: C-Br Bond Formation >
Synthesis of 1,2-bromoamines
Aziridines are opened regioselectively with hydrogen and lithium halides to yield β-haloamines in the presence of β-cyclodextrin using water as the solvent.
N. S. Krishnaveni, K. Surendra, M. Narender, Y. V. D. Nageswar, K. R. Rao, Synthesis, 2004, 501-502.
β-Functionalized sulfonamides were produced in good yields by the regioselective ring opening of N-tosylaziridines with trimethylsilylated nucleophiles, catalyzed by N,N,N',N'-tetramethylethylenediamine (TMEDA).
S. Minakata, Y. Okada, Y. Oderaotoshi, M. Komatsu, Org. Lett., 2005, 7, 3509-3512.
A new procedure for aminobromination of olefins gives vicinal bromoamine derivatives in high yields using Cu, Mn, or V catalysts with p-toluenesulfonamide as nitrogen source and N-bromosuccinimide (NBS) as bromine source. Excellent regio- and stereoselectivity is shown for different olefinic substrates as well as transition metal catalysts.
V. V. Thakur, S. K. Talluri, A. Sudalai, Org. Lett., 2003, 5, 861-864.
A convenient and efficient iron-catalyzed aminobromination of alkenes has been developed using inexpensive FeCl2 as the catalyst, amides/sulfonamides and NBS as the nitrogen and bromine sources, respectively, under mild conditions.
Z. Wang, Y. Zhang, H. Fu, Y. Jiang, Y. Zhao, Synlett, 2008, 2667-2668.
In an efficient, catalyst-free, and metal-free bromoamidation of unactivated olefins, 4-(trifluoromethyl)benzenesulfonamide and N-bromosuccinimide were used as the nitrogen and halogen sources, respectively. The methodology is applicable to both cyclic and aliphatic olefins.
W. Z. Yu, F. Chen, Y. A. Cheng, Y.-Y. Yeung, J. Org. Chem., 2015, 80, 2815-2821.
AgBF4 or InBr3/AgBF4 (1:3) as catalyst and N-halophthalimide as both nitrogen and halogen source enable a simple, efficient, and highly atom economic haloamidation of simple alkenes. A broad range of olefins afford vicinal haloamines in good yields and with high regioselectivity and diastereoselectivity.
L. Song, S. Luo, J.-P. Cheng, Org. Lett., 2013, 15, 5702-5705.