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Secondary role: Indole and pyrrole derivatives are alkylated with unactivated secondary aliphatic alcohols by a Brønsted acid-catalyzed redox chain reaction mechanism. Broad functional-group tolerance has been demonstrated and preliminary studies suggest that 1,4-reduction of a putative indolyl carbocation is the dominant mechanistic pathway.
1-Phenyl-1H-tetrazole-5-thiol 1 (PT-thiol) is employed in a unique Markovnikov-selective formal hydroamination of styrenyl compounds in the presence of catalytic amounts of Ga(OTf)3. This gives rise to the formation of tetrazolothione moieties in an atom-economical manner. Mechanistically, we have determined that this transformation may occur by kinetically(More)
Rational assembly of small molecule libraries for purposes of drug discovery requires an efficient approach in which the synthesis of bioactive compounds is enabled so that numerous structurally related compounds of a similar basic formulation can be derived. Here, we describe (4 + 3) and (3 + 2) indole annulation strategies that quickly generate complex(More)
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