Synthesis by Aromatization

Toyota, S.; Iwanaga, T.

doi:10.1055/sos-sd-045-00783

Cited by 1 publication

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“…The core skeleton of geminal diarylethylene is present in many pharmacophores, including tamoxifen, bexarotene, and ratanhine. − Among these, 1,1-diarylethylene derivatives, although the tricyclic 9-fluorenylidene system (also known as methylidenefluorene), exhibit key functionalized properties in advanced material chemistry. − Due to their potential applications, the development of a one-pot facile transition-metal-promoted synthetic route to produce these motifs has attracted significant attention, and many development attempts have been reported. The conventional synthetic route toward substituted alkylidene or benzylidene fluorenes is based on the Knoevenagel condensation of fluorene with aliphatic and aromatic aldehydes .…”

Section: Introductionmentioning

confidence: 99%

CuBr₂-Mediated One-Pot Synthesis of Sulfonyl 9-Fluorenylidenes

2020

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In this article, a high-yield method for the synthesis of sulfonyl 9fluorenylidenes is described, which consists of a one-pot straightforward three-step synthetic route, including (i) CuBr 2 -mediated α-bromination of o-arylacetophenone, (ii) sequential nucleophilic substitution of the resulting α-bromo o-arylacetophenone with sodium sulfinate (RSO 2 Na), and (iii) the CuBr 2 -mediated intramolecular Friedel−Crafts cyclizative dehydration. A plausible mechanism is proposed and discussed. This protocol provides a highly effective regio-and stereoselective annulation via the formation of one carbon−carbon (C−C) bond and one carbon−sulfur (C−S) bond.

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