Search: onr:"swepub:oai:DiVA.org:kth-316433" >
Highly congested sp...
Highly congested spiro-compounds via photoredox-mediated dearomative annulation cascade
-
- Zhou, Chao (author)
- KTH,Organisk kemi
-
- Shatskiy, Andrey, 1989- (author)
- KTH,Organisk kemi
-
- Temerdashev, Azamat Z. (author)
- Kuban State Univ, Dept Analyt Chem, Stavropolskaya St 149, Krasnodar 350040, Russia.
-
show more...
-
- Kärkäs, Markus D., 1984- (author)
- KTH,Organisk kemi
-
- Dinér, Peter (author)
- KTH,Organisk kemi
-
show less...
-
(creator_code:org_t)
- 2022-08-05
- 2022
- English.
-
In: Communications Chemistry. - : Springer Nature. - 2399-3669. ; 5:1
- Related links:
-
https://doi.org/10.1...
-
show more...
-
https://urn.kb.se/re...
-
https://doi.org/10.1...
-
show less...
Abstract
Subject headings
Close
- 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.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Publication and Content Type
- ref (subject category)
- art (subject category)
Find in a library
To the university's database