ChemInform Abstract: 3‐Sulfolenes and Their Derivatives: Synthesis and Applications

Brant, Michael G.; Wulff, Jeremy E.

doi:10.1002/chin.201612273

Cited by 2 publications

(2 citation statements)

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“…Moreover, 1-chloro-4-nitrobenzene proved to be a suitable substrate to give the desired product 84 in moderate yield. In addition, the protocol could be also utilized to synthesize annulated-sulfones, which are the most important motifs in pharmaceuticals 41 . By using alkene-tethered alkyl bromides as the starting materials, a variety of cyclic sulfones bearing four- to eight-membered rings were systematically prepared in moderate to excellent yields ( 85 – 96 , 59–92%), although some O -alkylated cyclization byproducts were detected under this transformation.…”

Section: Resultsmentioning

confidence: 99%

Iron-catalyzed fluoroalkylative alkylsulfonylation of alkenes via radical-anion relay

Hou,

Liu,

Huang

2024

Nat Commun

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Transition metal-catalyzed reductive difunctionalization of alkenes with alkyl halides is a powerful method for upgrading commodity chemicals into densely functionalized molecules. However, super stoichiometric amounts of metal reductant and the requirement of installing a directing group into alkenes to suppress the inherent β-H elimination bring great limitations to this type of reaction. We demonstrate herein that the difunctionalization of alkenes with two different alkyl halides is accessible via a radical-anion relay with Na2S2O4 as both reductant and sulfone-source. The Na2S2O4 together with the electron-shuttle catalyst is crucial to divert the mechanistic pathway toward the formation of alkyl sulfone anion instead of the previously reported alkylmetal intermediates. Mechanistic studies allow the identification of carbon-centered alkyl radical and sulfur-centered alkyl sulfone radical, which are in equilibrium via capture or extrusion of SO2 and could be converted to alkyl sulfone anion accelerated by iron electron-shuttle catalysis, leading to the observed high chemoselectivity.

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Section: Resultsmentioning

confidence: 99%

Iron-catalyzed fluoroalkylative alkylsulfonylation of alkenes via radical-anion relay

Hou,

Liu,

Huang

2024

Nat Commun

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“…Sulfolene and its derivatives are important building blocks in organic synthesis and also an integral part of many biologically active molecules. 9 In the C–H activation chemistry, sulfolene has never been used as a coupling partner. Therefore, we envisaged that sulfolene could be utilised as a coupling partner in the C–H activation reactions.…”

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confidence: 99%

Distal meta-C–H functionalization of α-substituted cinnamates

Bakthadoss

Reddy

2023

Chem. Sci.

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ChemInform Abstract: 3‐Sulfolenes and Their Derivatives: Synthesis and Applications

Abstract: 3-Sulfolenes and Their Derivatives: Synthesis and Applications -[76 refs. + subrefs.]. -(BRANT, M. G.; WULFF*, J. E.; Synthesis 48 (2016) 1, 1-17, http://dx.doi.org/10.1055/s-0035-1560351 ; Dep. Chem., Univ. Victoria, Victoria, B. C. V8W 3V6, Can.; Eng.) -Y. Steudel 12-273

Cited by 2 publications

References 1 publication

Iron-catalyzed fluoroalkylative alkylsulfonylation of alkenes via radical-anion relay

Iron-catalyzed fluoroalkylative alkylsulfonylation of alkenes via radical-anion relay

Distal meta-C–H functionalization of α-substituted cinnamates

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