Carbo- and heterocycles frequently serve as crucial scaffolds in drugs, natural products, fine chemicals, and biologically and pharmaceutically active compounds. Consequently, the development of general, practical, and efficient synthetic approaches...
A general and metal-free protocol for the construction
of benzo[b]fluorenyl thiophosphates was developed
through the cascade
cyclization of easily prepared diynols and (RO)2P(O)SH,
with water as the only byproduct. The novel transformation involved
the allenyl thiophosphate as the key intermediate, followed by Schmittel-type
cyclization to achieve the desired products. Notably, (RO)2P(O)SH acted not only as a nucleophile but also as an acid-promoter
to initiate the reaction.
An efficient and practical approach for the synthesis of triaryl allenyl sulfones from easily accessible propargylic alcohols was developed, by using sodium sulfinates as a sulfonyl source in the presence of Brønsted acid. The reaction proceeded via allenyl carbocation as the key intermediate and was followed by a nucleophilic attack of sodium sulfinates to produce allenyl sulfones in moderate to excellent yields.
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