Iminium and enamine catalysis in enantioselective photochemical reactions

Zou, You‐Quan; Hörmann, Fabian M.; Bach, Thorsten

doi:10.1039/c7cs00509a

Cited by 240 publications

(129 citation statements)

References 55 publications

(53 reference statements)

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“…Photoredox catalysis applies light as an energy source for organic reactions . Herein, we report an advanced photoredox catalytic method for the activation of SF 6 , which not only pentafluorosulfanylates α‐methyl‐ ( 1 ) and α‐phenyl‐ ( 2 ) styrenes but additionally forms a C−O bond, which significantly broadens the synthetic scope and opens the way for the functionalization of SF 5 building blocks.…”

Section: Figurementioning

confidence: 99%

Photoredox Catalytic α‐Alkoxypentafluorosulfanylation of α‐Methyl‐ and α‐Phenylstyrene Using SF₆

Rombach

Wagenknecht

2019

Angew Chem Int Ed

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SF6 was applied as pentafluorosulfanylation reagent to prepare ethers with a vicinal SF5 substituent through a one‐step method involving photoredox catalysis. This method shows a broad substrate scope with respect to applicable alcohols for the conversion of α‐methyl and α‐phenyl styrenes. The products bear a new structural motif with two functional groups installed in one step. The alkoxy group allows elimination and azidation as further transformations into valuable pentafluorosulfanylated compounds. These results confirm that non‐toxic SF6 is a useful SF5 transfer reagent if properly activated by photoredox catalysis, and toxic reagents are completely avoided. In combination with light as an energy source, a high level of sustainability is achieved. Through this method, the proposed potential of the SF5 substituent in medicinal chemistry, agrochemistry, and materials chemistry may be exploited in the future.

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Section: Figurementioning

confidence: 99%

Photoredox Catalytic α‐Alkoxypentafluorosulfanylation of α‐Methyl‐ and α‐Phenylstyrene Using SF₆

Rombach

Wagenknecht

2019

Angew Chem Int Ed

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“…Die Photoredoxkatalyse verwendet Licht als Energiequelle für organische Reaktionen . Wir berichten hier über eine fortschrittliche photoredoxkatalytische Aktivierung von SF 6 , die nicht nur α‐Methyl‐ ( 1 ) und α‐Phenylstyrol ( 2 ) pentafluorosulfanyliert, sondern zusätzlich eine C‐O‐Bindung ausbildet, wodurch die synthetisch zugänglicheStrukturvielfalt deutlich verbreitert und der Weg zur Funktionalisierung der SF 5 ‐Bausteine geöffnet wird.…”

Section: Figureunclassified

Photoredoxkatalytische α‐Alkoxypentafluorosulfanylierung von α‐Methyl‐ und α‐Phenylstyrol mithilfe von SF₆

Rombach

Wagenknecht

2019

Angewandte Chemie

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SF6 wurde als Pentafluorosulfanylierungsreagenz in der Photoredoxkatalyse verwendet, um über ein Einstufenprotokoll Ether mit vicinalem SF5‐Substituent herzustellen. Diese Methode weist ein breites Substratspektrum bei den verwendbaren Alkoholen für die Umsetzung von α‐Methyl‐ und α‐Phenylstyrol auf. Die Produkte enthalten ein neues Strukturmotiv mit zwei funktionellen Gruppen, das in einem Reaktionsschritt aufgebaut wird. Die Alkoxygruppe erlaubt die Eliminierung sowie die Umsetzung in ein Azid als weitere Transformationen in wertvolle pentafluorosulfanylierte Verbindungen. Diese Resultate bestätigen, dass das ungiftige SF6 ein nützliches SF5‐Transferreagenz darstellt, wenn es durch Photoredoxkatalyse unter den richtigen Bedingungen aktiviert wird, wodurch giftige Reagenzien vollständig vermieden werden. Kombiniert mit Licht als Energiequelle wird ein hoher Grad an Nachhaltigkeit erzielt. Über diesen synthetischen Zugang kann in Zukunft das vorhergesagte Potential des SF5‐Substituenten in der Medizinal‐, Agro‐ und Materialchemie erforscht werden.

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“…Many review articles covering this area have been published. [8] New concepts and strategies for controlling enantioselectivity in radical reactions are emerging continuously. Transition metal catalyzed asymmetric synthesis is one of the most versatile methods for preparing enantiomerically pure compounds and has developed into a practical synthetic paradigm.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Transition Metal‐Catalyzed Asymmetric Radical Reactions

Wang

Kong

2018

Chin. J. Chem.

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Control of enantioselectivity in radical reactions was a formidable challenge for organic chemists for decades. Thanks to the key role of transition metal complexes both in promoting and highly enantioselectively controlling sophisticated synthetic routes, great improvements in this filed have been achieved by merging transition‐metal asymmetric catalysis with radical chemistry. Herein we provide a perspective of some of the most significant contributions in the field during the past decades. Accordingly, the major advances are classified based on different strategies for controlling stereoselectivity including: (1) chiral metal complex chelation, (2) chiral metal complex combined with radical species and reductive elimination, (3) chiral metal complex outer‐sphere substitution by radical intermediate. Brief discussion of mechanism is presented whenever relevant.

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Iminium and enamine catalysis in enantioselective photochemical reactions

Abstract: The rapidly growing area of iminium and enamine catalysis in enantioselective photochemistry is reviewed, with an emphasis on catalytic modes and reaction types.

Cited by 240 publications

References 55 publications

Photoredox Catalytic α‐Alkoxypentafluorosulfanylation of α‐Methyl‐ and α‐Phenylstyrene Using SF₆

Photoredox Catalytic α‐Alkoxypentafluorosulfanylation of α‐Methyl‐ and α‐Phenylstyrene Using SF₆

Photoredoxkatalytische α‐Alkoxypentafluorosulfanylierung von α‐Methyl‐ und α‐Phenylstyrol mithilfe von SF₆

Recent Advances in Transition Metal‐Catalyzed Asymmetric Radical Reactions

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Iminium and enamine catalysis in enantioselective photochemical reactions

Abstract: The rapidly growing area of iminium and enamine catalysis in enantioselective photochemistry is reviewed, with an emphasis on catalytic modes and reaction types.

Cited by 240 publications

References 55 publications

Photoredox Catalytic α‐Alkoxypentafluorosulfanylation of α‐Methyl‐ and α‐Phenylstyrene Using SF6

Photoredox Catalytic α‐Alkoxypentafluorosulfanylation of α‐Methyl‐ and α‐Phenylstyrene Using SF6

Photoredoxkatalytische α‐Alkoxypentafluorosulfanylierung von α‐Methyl‐ und α‐Phenylstyrol mithilfe von SF6

Recent Advances in Transition Metal‐Catalyzed Asymmetric Radical Reactions

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Photoredox Catalytic α‐Alkoxypentafluorosulfanylation of α‐Methyl‐ and α‐Phenylstyrene Using SF₆

Photoredox Catalytic α‐Alkoxypentafluorosulfanylation of α‐Methyl‐ and α‐Phenylstyrene Using SF₆

Photoredoxkatalytische α‐Alkoxypentafluorosulfanylierung von α‐Methyl‐ und α‐Phenylstyrol mithilfe von SF₆