Encyclopedia of Reagents for Organic Synthesis 2006
DOI: 10.1002/047084289x.rb144.pub2
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1,8-Bis(dimethylamino)naphthalene

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“…[28] Borylation of N-methylindole afforded exclusively the 3-substituted regioisomer, in sharp contrast to the previously reported reaction with B(C 6 F 5 ) 3 , which produces the 2-borylated N-methylindole. [29] Pyrrole 15c gave a mixture of mono-borylated regioisomers along with some of the diborylated 16c using one equivalent of 8a (ca.…”
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“…[28] Borylation of N-methylindole afforded exclusively the 3-substituted regioisomer, in sharp contrast to the previously reported reaction with B(C 6 F 5 ) 3 , which produces the 2-borylated N-methylindole. [29] Pyrrole 15c gave a mixture of mono-borylated regioisomers along with some of the diborylated 16c using one equivalent of 8a (ca.…”
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“…In principle, these requirements might be satisfied by 1,8-bis(dimethylamino)naphthalene (1), a hindered and exceptionally basic aniline that finds numerous applications as a basic catalyst or reagent due to its legendary lack of nucleophilicity. [2,3] Strong electrophiles interact weakly, if at all, with the amine nitrogens, and very few examples are known where stable bonds to nitrogen can be formed between 1 and electrophilic groups larger than hydrogen. [2,[4][5][6][7] Among these exceptional cases, cyclic boronium structures 2 and 3 are relatively stable because the subunits BH 2 and BF 2 have minimal steric requirements.…”
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