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3CN is the most common and suitable reagent used to generate arynes from their precursor 2-(trimethylsilyl)-phenyl triflates.
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21
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0001347811
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27844442610
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Since the completion of this work, an article has appeared which describes a synthesis of triphenylene. According to the single example presented in the paper, aryne 1b reacted with 2b to yield the corresponding triphenylene in only 50% yield. It is noteworthy that our method, utilizing a suitable additive and thereby milder, reproducible conditions, afforded triphenylenes in very good yields. Moreover, aryne 1a was also successfully employed. See: Z. Liu, X. Zhang and R. C. Larock, J. Am. Chem. Soc., 2005, 127, 15716.
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32844474961
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note
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Even though there is much precedence for the generation of arynes from precursors 1, we carried out a reaction with an unsymmetrical aryne 4-methyl-2-trimethylsilylaryltriflate with 2a. A mixture of regioisomers, as expected for a reaction of 4-methylbenzyne, was obtained, thereby confirming the involvement of arynes in this reaction.
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