Synthesis of 1‑Aryltetralins and 1‑Arylnaphthalenes via (4 + 2) Annulation of β‑Ketosulfones with Styryl Bromides

Synthesis of 1‑Aryltetralins and 1‑Arylnaphthalenes via (4 + 2) Annulation of β‑Ketosulfones with Styryl Bromides

A novel route has been developed for the synthesis of various substituted 1-aryltetralins 6 and 1-arylnaphthalenes 8 via (1) K2CO3-mediated α-styrylation of β-ketosulfones 3 with bromostyryl bromides 4 and (2) stereocontrolled NaBH4-promoted reduction of the resulting γ-alkenones 5, followed by BF3·...

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Veröffentlicht in:Organic letters 2016-04, Vol.18 (7), p.1682-1685
Hauptverfasser: Chang, Meng-Yang, Cheng, Yu-Chieh
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container_title Organic letters
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creator Chang, Meng-Yang
Cheng, Yu-Chieh
description A novel route has been developed for the synthesis of various substituted 1-aryltetralins 6 and 1-arylnaphthalenes 8 via (1) K2CO3-mediated α-styrylation of β-ketosulfones 3 with bromostyryl bromides 4 and (2) stereocontrolled NaBH4-promoted reduction of the resulting γ-alkenones 5, followed by BF3·OEt2-catalyzed intramolecular annulation of the corresponding γ-alkenols 7 under rt/5 h and reflux/10 h conditions, respectively. The key structures of 6 and 8 were confirmed by X-ray crystallographic analysis. A plausible mechanism has been proposed.
doi_str_mv 10.1021/acs.orglett.6b00603
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title Synthesis of 1‑Aryltetralins and 1‑Arylnaphthalenes via (4 + 2) Annulation of β‑Ketosulfones with Styryl Bromides
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