Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan.
J Org Chem. 2020 Jun 5;85(11):6897-6909. doi: 10.1021/acs.joc.0c00035. Epub 2020 May 15.
In this article, a high-yield method for the synthesis of sulfonyl 9-fluorenylidenes is described, which consists of a one-pot straightforward three-step synthetic route, including (i) CuBr-mediated α-bromination of -arylacetophenone, (ii) sequential nucleophilic substitution of the resulting α-bromo -arylacetophenone with sodium sulfinate (RSONa), and (iii) the CuBr-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.
本文描述了一种高产率合成磺酰基 9-芴基烯的方法，该方法包括一锅直接三步合成路线，包括(i)CuBr 介导的-芳基苯乙酮的α-溴化，(ii)所得α-溴-芳基苯乙酮与亚硫酸钠（RSONa）的顺序亲核取代，以及(iii)CuBr 介导的分子内傅-克环化脱水。提出并讨论了一种合理的机制。该方案通过形成一个碳-碳（C-C）键和一个碳-硫（C-S）键，提供了一种高效的区域和立体选择性环化。
