Categories: C-Br Bond Formation >
Synthesis of alkynyl bromides
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The use of chloramine-B as the oxidant and KI or NaBr as the halogen source
enables a direct oxidative halogenation of terminal alkynes to provide
synthetically valuable 1-iodoalkynes and 1-bromoalkynes in very good yields
under mild reaction conditions.
X. Liu, G. Chen, C. Li, P. Liu, Synlett, 2018, 29,
2051-2055.
Using triethylamine as catalyst in Hunsdiecker reactions with N-halosuccinimides
as Br+ or I+ source, cinnamic acids, and propiolic acids are
converted to the corresponding α-halostyrenes and 1-halo-1-alkynes in good isolated yields within 1-5 min.
J. Prakash, S. Roy, J. Org. Chem.,
2002, 67, 7861-7864.
Organotrifluoroborates are rapidly and regioselectively converted into
organic bromides in excellent yields under mild conditions, using sodium
bromide in the presence of chloramine-T.
G. W. Kabalka, A. R. Mereddy, Organometallics, 2004,
23, 4519-4521.