DOI: 10.1002/chem.201101047. α‐Sulfonyl Succinimides: Versatile Sulfinate Donors in Fe‐Catalyzed, Salt‐Free, Neutral Allylic Substitution

α‐Sulfonyl Succinimides: Versatile Sulfinate Donors in Fe‐Catalyzed, Salt‐Free, Neutral Allylic Substitution

10.1002/chem.201101047

Crossref journal-article

Wiley

Chemistry – A European Journal (311)

Abstract

AbstractAllyl sulfones are versatile intermediates in organic chemistry. The presence of two distinct functional groups sets the stage for a plethora of subsequent transformations. However, despite these advantages the preparation of regioisomerically enriched sulfones is not easy. The use of sulfinate salts as nucleophiles in substitutions is frequently accompanied by side reactions such as π‐bond migration, β‐elimination, and so on. Herein we present a preparatively simple way to synthesize a variety of different aryl or alkyl allyl sulfones starting from readily accessible allylic carbonates. By employing aryl or alkyl α‐sulfonyl succinimides as sulfinate synthons, mild and regioselective ipso substitution of diverse allylic carbonates was realized.

Bibliography

Jegelka, M., & Plietker, B. (2011). Î±âSulfonyl Succinimides: Versatile Sulfinate Donors in FeâCatalyzed, SaltâFree, Neutral Allylic Substitution. Chemistry â A European Journal, 17(37), 10417â10430. Portico.

Authors 2

Markus Jegelka (first)
Bernd Plietker (additional)

References 71 Referenced 62

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Dates

Type	When
Created	14 years, 1 month ago (Aug. 4, 2011, 12:34 p.m.)
Deposited	1 year, 10 months ago (Oct. 16, 2023, 3:45 p.m.)
Indexed	4 weeks, 2 days ago (Aug. 6, 2025, 8:50 a.m.)
Issued	14 years, 1 month ago (Aug. 4, 2011)
Published	14 years, 1 month ago (Aug. 4, 2011)
Published Online	14 years, 1 month ago (Aug. 4, 2011)
Published Print	14 years ago (Sept. 5, 2011)

Funders 0

None

BibTeX

@article{Jegelka_2011, title={α‐Sulfonyl Succinimides: Versatile Sulfinate Donors in Fe‐Catalyzed, Salt‐Free, Neutral Allylic Substitution}, volume={17}, ISSN={1521-3765}, url={http://dx.doi.org/10.1002/chem.201101047}, DOI={10.1002/chem.201101047}, number={37}, journal={Chemistry – A European Journal}, publisher={Wiley}, author={Jegelka, Markus and Plietker, Bernd}, year={2011}, month=aug, pages={10417–10430} }

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