2022
DOI: 10.26434/chemrxiv-2022-28crb
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A general alkene aminoarylation enabled by N-centered radical reactivity of sulfinamides

Abstract: We disclose an intermolecular 1,2-aminoarylation of alkenes using aryl sulfinamide reagents as bifunctional amine and arene donors. This reaction features excellent regio- and diastereoselectivity on a variety of activated and unactivated substrates. Using a weakly oxidizing photoredox catalyst, a sulfinamidyl radical is generated under mild conditions and adds to an alkene to form a new C–N bond. A desulfinylative Smiles-Truce rearrangement follows to form a new C–C bond. In this manner, biologically active a… Show more

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Cited by 4 publications
(3 citation statements)
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“…An elegant light-mediated intermolecular aminoarylation of alkenes using arylsulfonylacetamides as bifunctional reagents has been demonstrated [40][41][42][43] . The reaction, only applicable to electron-rich styrenes, furnished the corresponding β,β-diarylethylamines in racemic form 40 .…”
Section: Introductionmentioning
confidence: 99%
“…An elegant light-mediated intermolecular aminoarylation of alkenes using arylsulfonylacetamides as bifunctional reagents has been demonstrated [40][41][42][43] . The reaction, only applicable to electron-rich styrenes, furnished the corresponding β,β-diarylethylamines in racemic form 40 .…”
Section: Introductionmentioning
confidence: 99%
“…In our previous work, we designed a general methodology for the aminoarylation reaction of unactivated alkenes using sulfinamides as precursors for nitrogen-centered radicals (NCRs) (Scheme 2a). [13] In that work, the NCR was trapped by the unactivated alkene, leading to the Smiles-Truce rearrangements. We had hypothesized divergent reactivity can be achieved when alternative radical acceptors are employed (Scheme 2b).…”
mentioning
confidence: 99%
“…[15] The details of the mechanism are still under investigation, however, work conducted thus far has led us to believe we can develop conditions to favor and capture this postulated sulfur-centered radical (SCR) for identification and subsequent reactivity. Results and discussion: Inspired by our prior research on the aminoarylation reaction involving unactivated alkenes and the use of sulfinamides as precursors for NCRs (Scheme 2a), [13] we envisioned synthesizing enamines by employing alkenes bearing leaving groups (Scheme 2c). We hypothesized the generation of a NCR that would perform an addition reaction with a vinyl halide followed by a rapid elimination to the enamine.…”
mentioning
confidence: 99%

A modular photoredox route towards sulfoximines

Glossbrenner,
González-Granda,
Nayal
et al. 2023
Preprint