Abstract

Tetraarylethylenes exhibit intriguing photophysical properties and sulfur atom frequently play a vital role in organic photoelectric materials and biologically active compounds. Tetrasubstituted vinyl sulfides, which include both sulfur atom and tetrasubstituted alkenes motifs, might be a suitable skeleton for the discovery of the new material molecules and drug with unique functions and properties. However, how to modular synthesis these kinds of compounds is still challenging. Herein, a chemo- and stereo-selective Rh(II)-catalyzed [1,4]-acyl rearrangements of α-diazo carbonyl compounds and thioesters has been developed, providing a modular strategy to a library of 63 tetrasubstituted vinyl sulfides. In this transformation, the yield is up to 95% and the turnover number is up to 3650. The mechanism of this reaction is investigated by combining experiments and density functional theory calculation. Moreover, the “aggregation-induced emission” effect of tetrasubstituted vinyl sulfides were also investigated, which might useful in functional material, biological imaging and chemicalnsing via structural modification.

Highlights

  • Tetraarylethylenes exhibit intriguing photophysical properties and sulfur atom frequently play a vital role in organic photoelectric materials and biologically active compounds

  • In this work, based on our continuous interest in transitionmetal catalyzed carbene transfer reaction of α-diazo carbonyl compounds57–59, we describe that structurally diverse tetrasubstituted vinyl sulfides (TVSs) are modularly assembled for the first time by a rhodium-catalyzed ylide formation/[1,4]

  • The results indicated the substituents on diazo compounds 2 were vital for the aggregation-induced emission” (AIE)-activity of the producing vinyl sulfides

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Summary

Introduction

Tetraarylethylenes exhibit intriguing photophysical properties and sulfur atom frequently play a vital role in organic photoelectric materials and biologically active compounds. A chemo- and stereo-selective Rh(II)-catalyzed [1,4]-acyl rearrangements of α-diazo carbonyl compounds and thioesters has been developed, providing a modular strategy to a library of 63 tetrasubstituted vinyl sulfides In this transformation, the yield is up to 95% and the turnover number is up to 3650. Especially α-diazocarbonyl compounds which are prepared and handled, are highly important reagents in synthetic chemistry, because they have high and versatile reactivity which have been used in a series of carbene transfer reactions including X-H (X = O, N, S, C, etc.) insertion, cyclopropanation, and ylide formation under the catalysis of transition metals32–37 They are used frequently for the synthesis of sulfides via the construction of C–S bond. In this work, based on our continuous interest in transitionmetal catalyzed carbene transfer reaction of α-diazo carbonyl compounds, we describe that structurally diverse tetrasubstituted vinyl sulfides (TVSs) are modularly assembled for the first time by a rhodium-catalyzed ylide formation/[1,4]-

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Conclusion

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