Benzylic bromination catalyzed by triphenylphosphine selenide via Lewis basic activation
2017
Abstract The synthesis of benzyl bromides was achieved under mild reaction conditions using N -bromosuccinimide as a bromine source and triphenylphosphine selenide as a catalyst. These conditions were compatible with a variety of substrates including boronic esters, protected amines to give imines, and carboxylic acids (to give phthalides when ortho to the benzylic center). A preliminary mechanistic investigation utilizing calculated bond dissociation energies (BDE) is employed to rationalize how a Lewis base can activate a radical mechanism.
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