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35.2.5.2.6 Method 6: Hydrobromination of Epoxides Using Bromo(imido)metal Complexes

DOI: 10.1055/sos-SD-035-00442

Rück-Braun, K.; Freysoldt, T.Science of Synthesis, (200735510.

Beside magnesium bromide, other metal catalysts are able to induce a regioselective ring opening of epoxides by chelation. An imidochromium complex [CrBr3(N-t-Bu)(DME)] is able to open epoxide 32 with good regioselectivity (Scheme 14).[‌44‌] The complex can be used stoichiometrically, or catalytically with bromotrimethylsilane, as a ring-opening reagent to yield bromo alcohols 33 and 34. Better regioselectivity is achieved in reactions without bromotrimethylsilane, although no experimental procedure is given in the literature.

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