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Highly congested sp...
Highly congested spiro-compounds via photoredox-mediated dearomative annulation cascade
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- Zhou, Chao (författare)
- KTH,Organisk kemi
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- Shatskiy, Andrey, 1989- (författare)
- KTH,Organisk kemi
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- Temerdashev, Azamat Z. (författare)
- Kuban State Univ, Dept Analyt Chem, Stavropolskaya St 149, Krasnodar 350040, Russia.
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- Kärkäs, Markus D., 1984- (författare)
- KTH,Organisk kemi
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- Dinér, Peter (författare)
- KTH,Organisk kemi
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(creator_code:org_t)
- 2022-08-05
- 2022
- Engelska.
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Ingår i: Communications Chemistry. - : Springer Nature. - 2399-3669. ; 5:1
- Relaterad länk:
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https://doi.org/10.1...
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- Photo-mediated radical dearomatization involving 5-exo-trig cyclizations has proven to be an important route to accessing spirocyclic compounds, whereas 6-exo-trig spirocyclization has been much less explored. In this work, a dearomative annulation cascade is realized through photoredox-mediated C-O bond activation of aromatic carboxylic acids to produce two kinds of spirocyclic frameworks. Mechanistically, the acyl radical is formed through oxidation of triphenylphosphine and subsequent C-O bond cleavage, followed by a 6-exo-trig cyclization/SET/protonation sequence to generate the spiro-chromanone products in an intramolecular manner. Furthermore, the protocol was extended to more challenging intermolecular tandem sequences consisting of C-O bond cleavage, radical addition to an alkene substrate, and 5-exo-trig cyclization to yield complex spirocyclic lactams. Photo-mediated radical dearomatization involving 5-exo-trig cyclizations has proven to be an important route to accessing spirocyclic compounds, whereas 6-exo-trig spirocyclization has been much less explored. Here, a dearomative annulation cascade is realized through a photoredox-mediated C-O bond activation of aromatic carboxylic acids to produce two kinds of spirocyclic frameworks, whereby the spirocyclizations are triggered by acyl radical formation from benzoic acids leading to spiro-chromanones via a direct intramolecular 6-exo-trig cyclization or spirocyclic lactams via an intermolecular addition/5-exo-trig cyclization cascade.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
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