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Cycloaddition of benzyne to the perylene bay region: synthesis of naphtho[ghi]perylene [167,168,169]. Reagents and conditions: (a) benzenediazonium 2-carboxylate, DCM/THF (4v/1v), rfx, 3.5 h, Y = 66%; (b) NBu4F trihydrate (TBAF), 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (benzyne precursor), PhMe, rfx, 2.5 h, Y = 45%; and (c) phthalic anhydride (benzyne precursor), high-temperature flow system (up to 1000 °C), Y = 4.8%.
