Construction of 3-Sulfonyl Naphthalenes via Tandem Reaction of 1,4-Diyn-3-yl Esters with Sodium Sulfinates

Abstract

Polysubstituted 3-sulfonyl naphthalenes were constructed in good to high yields by AlCl 3 -mediated tandem reaction of 1,4-diyn-3-yl esters and sodium sulfinates. This reaction proceeded under mild reaction conditions and tolerated a variety of functional groups. Moreover, the mechanistic studies indicated that the initial formation of allene under DBU from 1,4-diyn-3-yl ester and a sequence of nucleophilic addition of sodium sulfinate, the formation of allene, and intramolecular cyclization might be involved.

One‐Pot Access to Sulfonyl 2,3‐Diarylnaphthalenes via tBuOK‐Mediated Benzannulation of o‐Bis‐sulfonylmethyl Arenes with Diarylacetylenes

“…Functionalized arylnaphthalenes are important structural scaffolds in a number of versatile synthetic intermediates and natural products, [1] and they exhibit a wide range of potential bioactivities, [2][3] with examples such as justicidin B, [4a] taiwanin C [4b] and diphyllin. [4c] Based on the biological properties [5] and synthetic applications [6] of sulfonyl-conjugated substituents, the development of novel synthetic routes [7] and bioactive behaviors [8] of sulfonyl-containing arylnaphthalenes have attracted considerable research attention. Herein, based on the reported literature and our previous investigation [9] of naphthalene synthesis, one-pot tBuOK-mediated benzannulation of sulfonyl 2,3-diarylnaphthalenes was developed.…”

Construction of Fully Substituted Cyclobutanes by Tandem Reaction of 1,4-Diyn-3-ols and Anhydrides

“…Notably, the interesting 1,2-dimethylenecyclobutanes could be also synthesized successfully via [2+2] cycloaddition of in situ-generated allene intermediates from alkynes (Scheme c) . Recently, we reported the construction of naphthalene derivatives from 1,4-diyn-3-yl esters via allene species . Therefore, with our continuing interest in the application of alkynes in organic synthesis, we wonder whether the formation of bismethylenecyclobutane rings can be realized via tandem reaction of 1,4-diyn-3-ols and anhydrides under mild and benign reaction conditions, thus providing a practical and efficient synthesis of functionalized cyclobutane derivatives.…”