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Palladium pincer complex-catalyzed condensation of sulfonimines and isocyanoacetate to imidazoline derivatives. Dependence of the stereoselectivity on the ligand effects
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för fysikalisk kemi, oorganisk kemi och strukturkemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
2007 (Engelska)Ingår i: Advanced Synthesis & Catalysis, ISSN 1615-4150, Vol. 349, nr 17-18, s. 2585-2594Artikel i tidskrift (Refereegranskat) Published
Ort, förlag, år, upplaga, sidor
2007. Vol. 349, nr 17-18, s. 2585-2594
Identifikatorer
URN: urn:nbn:se:su:diva-10493DOI: 10.1002/adsc.200700242ISI: 000251737500008OAI: oai:DiVA.org:su-10493DiVA, id: diva2:177012
Anmärkning
Part of urn:nbn:se:su:diva-8524Tillgänglig från: 2008-12-12 Skapad: 2008-12-12 Senast uppdaterad: 2009-05-25Bibliografiskt granskad
Ingår i avhandling
1. Novel Pincer Complex-Catalyzed Transformations: Including Asymmetric Catalysis
Öppna denna publikation i ny flik eller fönster >>Novel Pincer Complex-Catalyzed Transformations: Including Asymmetric Catalysis
2009 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

This thesis is focused on the development of new pincer complex-catalyzed transformations. Optimization of the catalytic properties (fine-tuning) was directed to increase the catalytic activity as well as the chemo-, stereo- and enantioselectivity of the complexes. This was achieved by varying the heteroatoms in the terdentate pincer ligand, by changing the electronic properties of the coordinated aryl moiety and by implementing chiral functionalities in the pincer complexes.

In the cross-coupling reaction of vinyl epoxides and aziridines with organoboronic acids the chemoselectivity of the reaction could be increased by employment of pincer complexes instead of commonly used Pd(0) catalysts. Furthermore, the introduction of a methoxy substituent in the aromatic subunit of the complex considerably increased the activity of the pincer complex catalyst.

Fine-tuning of the enantioselectivity in electrophilic allylation reactions was achieved by using a wide variety of new BINOL- and biphenanthrol-based pincer complexes. The highest enantioselectivity (85% ee) was obtained by applying biphenanthrol-based pincer complexes.

Stereoselective pincer complex-catalyzed condensation of sulfonylimines with isocyanoacetate could be achieved under mild reaction conditions. By application of chiral PCP catalysts, 2-imidazolines could be obtained with up to 86% ee.

A new pincer complex-catalyzed C-H bond functionalization based reaction between organonitriles and sulfonylimines affords homoallylic amines and beta-aminonitriles in high yields. The asymmetric version of this process affords beta-aminonitriles with up to 71% ee.

In the last chapter, a pincer complex-catalyzed redox coupling reaction is described. In this highly regio- and stereoselective process the integrity of the pincer catalysts is fully retained. This catalytic reaction proceeds with a high level of functional group tolerance, as allylic acetate and aryl halide functionalities are retained.

Ort, förlag, år, upplaga, sidor
Stockholm: Institutionen för organisk kemi, 2009. s. 136
Nyckelord
pincer, palladium, catalysis, chiral, asymmetric, palladium IV, allylation, aldol, aminoacid, C-H functionalization, cross-coupling, homoallylic, heck reaction, tridentate ligand
Nationell ämneskategori
Kemi
Forskningsämne
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-8524 (URN)978-91-7155-825-1 (ISBN)
Disputation
2009-03-20, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00 (Engelska)
Opponent
Handledare
Tillgänglig från: 2009-02-26 Skapad: 2009-02-17 Senast uppdaterad: 2009-05-25Bibliografiskt granskad

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Aydin, JuhanesEriksson, Lars
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Institutionen för organisk kemiInstitutionen för fysikalisk kemi, oorganisk kemi och strukturkemi

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