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In general, the rates for amination of bromobenzene, 1-bromonaphthalene, and 3-bromopyridine were faster than those for amination of brominated [2.2]paracyclophanes. The reaction of 3-bromopyridine with benzhydrylideneamine in toluene occurred to completion after 2 h at 110 °C in 96% yield with the catalytic system (0.5% Pd-DPPF and 0.5% 3a). Under the same reaction condition, reaction of benzhydrylideneamine with bromobenzene and 1-bromonaphthalene occurred to completion in 93% and 94% yield within only 3 and 5 h.
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