A general, yet efficient synthesis method of 9-arylfluorenes via metal-free reductive coupling of N-tosylhydrazones and arylboronic acids has been developed. This methodology is realized by a one-pot protocol in two steps involving the preparation of N-tosylhydrazones by reacting tosylhydrazide with 9-fluorenone derivatives, followed by the reductive coupling of arylboronic acid in the presence of potassium carbonate to afford various 9-arylfluorenes analogues in moderate to excellent yields. Importantly, the catalytic system presented here enables the use of easily accessible starting materials and can be employed on a wide variety of substrates with good functional group tolerance. This protocol could also be particularly useful for the synthesis of 9-fluorenyl-substituted carbazolyl compounds.

The rapid and efficient KI/H₂O₂-mediated 2-sulfonylation of substituted indoles and N-methylpyrrole was established.

We report a C3–H direct iodination of pyrrolo[1,2-a]quinoxalines with TBAI or I₂; a series of novel 3-iodopyrrolo[1,2-a]quinoxaline derivatives were obtained with excellent regioselectivity and broad substrate scope. Mechanism studies show that a catalytic amount of p-toluenesulfonic acid significantly promotes the selectivity and conversion of the reaction. Notably, the reaction can be performed on a gram scale, and the iodinated products can be further transformed into potentially biologically active pyrrolo[1,2-a]quinoxaline derivatives by palladium-catalyzed coupling reactions.