Eine verbesserte Cyclooctyn-Synthese

Buhl, H.; Gugel, Hansjörg; Kolshorn, Heinz; Meier, Herbert

doi:10.1055/s-1978-24803

Cited by 43 publications

(9 citation statements)

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“…19,20 These systems are relatively easy to synthesize and can be derivatized at various aryl positions to enhance kinetics or solubility. As with many of these types of reagents, solubility is a significant hurdle in utility.…”

Section: Design Of Bioorthogonal Reagentsmentioning

confidence: 99%

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Cu-free click cycloaddition reactions in chemical biology

2010

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Bioorthogonal chemical reactions are paving the way for new innovations in biology. These reactions possess extreme selectivity and biocompatibility, such that their participating reagents can form covalent bonds within richly functionalized biological systems—in some cases, living organisms. This tutorial review will summarize the history of this emerging field, as well as recent progress in the development and application of bioorthogonal copper-free click cycloaddition reactions.

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Section: Design Of Bioorthogonal Reagentsmentioning

confidence: 99%

“…34 Protection of the alcohol followed by bromination gave dibromide 49 19. The strained alkyne was installed by dehydrobromination, and linkage of a probe to the free alcohol was achieved by way of a carbamate to give 50 .…”

Section: Synthesis Of Bioorthogonal Reagentsmentioning

confidence: 99%

Cu-free click cycloaddition reactions in chemical biology

2010

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“…[35][36][37] This led us to explore polymerization methods that do not involve the use of transition-metal catalysts,i ncluding reactions such as the Wittig,H orner-Wadsworth-Emmons, [38][39][40] Aza-Wittig, [41,42] and Knoevenagel condensation, [43] as well as Schiff-base formation. [50][51][52][53][54] In our hands,t he synthetic approach based on aWittig-PrØvost homologation sequence was found to be compatible with initial introduction of aryl halides (in this case,i odides), which could subsequently be converted into the required amines in the target monomer 6 (DIBO-(NH 2 ) 2 ). Amongst these,S chiff-base formation offers several advantages:i thas been well-explored, [46][47][48] can produce high-molecular-weight polymers,a nd the installation of amine groups is straightforward to achieve by using Buchwald-Hartwig chemistry.…”

Section: Conjugated Polymers Have Attracted Tremendous Attentionmentioning

confidence: 99%

“…[49] Thestructurally most simple parent structure,dibenzocyclooctyne (DIBO), [50] is ideal as am onomer for conjugated polymer synthesis because it has ar elatively planar, symmetrical structure. [49] In situ generation of the enol triflate followed by elimination using KHMDS formed the cyclooctyne 5, [54,57] and finally deprotection under aqueous acidic conditions allowed the isolation of monomer 6.T he comonomer,analkoxybenzene dialdehyde (9), was synthesized from bis(hexadecyloxy)diiodobenzene through am odified Bouveault aldehyde synthesis (Scheme 1b). As illustrated in Scheme 1, starting with dibenzosuberone,s tandard iodination conditions generated diiodosuberone 1 in modest yield.…”

Section: Conjugated Polymers Have Attracted Tremendous Attentionmentioning

confidence: 99%

Click Functionalization of a Dibenzocyclooctyne‐Containing Conjugated Polyimine

2015

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A conjugated poly(phenyl-co-dibenzocyclooctyne) Schiff-base polymer, prepared through polycondensation of dibenzocyclooctyne bisamine (DIBO-(NH2)2) with bis(hexadecyloxy)phenyldialdehyde, is reported. The resulting polymer, which has a high molecular weight (M(n)>30 kDa, M(w)>60 kDa), undergoes efficient strain-promoted alkyne-azide cycloaddition reactions with a series of azides. This enables quantitative modification of each repeat unit within the polymer backbone and the rapid synthesis of a conjugated polymer library with widely different substituents but a consistent degree of polymerization (DP). Kinetic studies show a second-order reaction rate constant that is consistent with monomeric dibenzocyclooctynes. Grafting with azide-terminated polystyrene and polyethylene glycol monomethyl ether chains of varying molecular weight resulted in the efficient syntheses of a series of graft copolymers with a conjugated backbone and maximal graft density.

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“…Dieses Phanomen ist auf eine Inversion der para-Briicke zuriickzufiihren und ist ein charakteristisches Merkmal der [6] 7. 150.4,146.9,60.7,51.7,31.6,28.9,28.7,28.4,27.6; 8,151.2,147.7,61.1,51.5,33.2,29.2,28.5, 28.4,27.6, 26.5 3,151.1,148.5.61.5,51.6,28.4,28.0,25.7,25.1,24.5,23.6; 8,152.3,147.1.61.3,51.6,26.7,26.6,26.2,25.3,24.1,23.8;IR(CDC1,) 9, 143.3, 139.0, 128.9, 52.2, 31.4, 30.8, 29.4, 27.2, 26.6;IR(CDC1,): ? [cm-'] = 2920, 2848, 1725, 1435, 1300, 1210, 1174 6, 142.4, 138.1, 130.9, 52.8, 32.1, 31.2, 30.6, 28.0, 27.2, 26.7 7, 57.0, 51.0, 42.2, 32.2, 30.8, 24.5; Angew.…”

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