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Carbocations as Lewis Acid Catalysts: Scope and Reactivity
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
2015 (engelsk)Inngår i: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 357, nr 1, s. 148-158Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

One class of potential Lewis acids that has received negligible attention as a catalyst is the carbocation. Here we show the potential of triarylmethylium ions as highly powerful Lewis acid catalysts for organic reactions. The Lewis acidity of the triarylmethylium ion can be easily tuned by variation of the electronic properties of the aromatic rings and the catalytic activity of the carbocation is shown to correlate directly to the level of stabilization of the empty p(C)-orbital at the cationic carbon. The versatility of triarylmethylium ions as efficient Lewis acid catalysts for organic reactions is demonstrated in Diels-Alder, aza-Diels-Alder, conjugate addition, halogenation, epoxide rearrangement and intramolecular hetro-ene reactions.

sted, utgiver, år, opplag, sider
2015. Vol. 357, nr 1, s. 148-158
Emneord [en]
carbocations, catalysis, Lewis acids, organocatalysis, trityl group
HSV kategori
Identifikatorer
URN: urn:nbn:se:kth:diva-144522DOI: 10.1002/adsc.201400609ISI: 000347705400018Scopus ID: 2-s2.0-84920733647OAI: oai:DiVA.org:kth-144522DiVA, id: diva2:713894
Merknad

Updated from manuscript to article.

QC 20150306

Tilgjengelig fra: 2014-04-24 Laget: 2014-04-24 Sist oppdatert: 2017-12-05bibliografisk kontrollert
Inngår i avhandling
1. Metal-Free Catalysis for Efficient Synthesis
Åpne denne publikasjonen i ny fane eller vindu >>Metal-Free Catalysis for Efficient Synthesis
2014 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

The strength of efficient metal-free catalysis will be examined in this thesis. Efforts towards more sustainable processes will be demonstrated through implementation of strategies that meet several of the 12 principles of Green Chemistry.In the first part, a stereoselective total synthesis of multiple alkaloids from the Corynantheine and Ipecac families together with their non-natural analogues will be disclosed. A highly efficient, common synthetic strategy is applied leading to high overall yields starting from easily available starting material. Overall operational simplicity and sustainability have been the main focus. Time-consuming and waste-generating isolations and purifications of intermediates have been minimized, as well as the introduction of protection-group chemistry. Moreover, the first example of the total synthesis of Hydroxydihydrocorynantheol together with its non-natural epimer has been accomplished in multi-gram scale without protection groups and without a single isolation or purification step in high overall yield and diastereoselectivity.In the second part, carbocations will be presented as highly effective and versatile non-metal Lewis acid catalysts. Lewis acidity-tuning of carbocations will be introduced and applied in several reactions to suppress competing reactions. Finally, the broad scope of carbocation catalyzed transformations will be exposed.At large, evident progress has been made towards more sustainable chemistry.

sted, utgiver, år, opplag, sider
KTH Royal Institute of Technology, 2014. s. 69
Serie
TRITA-CHE-Report, ISSN 1654-1081 ; 2014:15
Emneord
Homogeneous c atalysi s, O rga nocatalysis, Green C hemistry, T o tal S ynthesis, A lkaloids, A symmetric S ynthesis, N on - metal Lewis acid s, C arbocations, Sustainability
HSV kategori
Forskningsprogram
Kemi
Identifikatorer
urn:nbn:se:kth:diva-144577 (URN)978-91-7595-110-2 (ISBN)
Disputas
2014-05-08, E3, Osquars Backe 14, 5 tr, Stockholm, 13:00 (engelsk)
Opponent
Veileder
Merknad

QC 20140425

Tilgjengelig fra: 2014-04-25 Laget: 2014-04-24 Sist oppdatert: 2014-04-25bibliografisk kontrollert

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