Sonogashira cross-couplings using biocompatible conditions in water

Dibowski, Harald; Schmidtchen, Franz P.

doi:10.1016/s0040-4039(97)10674-8

Cited by 60 publications

(16 citation statements)

References 13 publications

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“…It is also compatible with attachment to proteins (19), via their lysine side chains, without alteringthe charge state on the amine functionality. Alloc removal using Pd[0] may be effected under aqueous conditions (20,21), in addition biocompatible Pd[0] Sonogashira couplings are reported (22). Our novel derivative may find therefore find use as an alternative biotinylation reagent for proteins.…”

Section: Discussionmentioning

confidence: 99%

A Stable Bis-Allyloxycarbonyl Biotin Aldehyde Derivative for Biotinylation via Reductive Alkylation: Application to the Synthesis of a Biotinylated Doxorubicin Derivative

et al. 2002

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A novel, stable, biotin aldehyde derivative is reported in which the biotin moiety is N1,N3-protected by the allyloxycarbonyl group. The derivative is stable to sodium cyanoborohydride mediated reductive alkylation and is cleaved under mild Pd [0] catalysis. This novel biotin aldehyde should have wide application in avidin- and streptavidin-based detection systems and bioassays. The derivative is utilized in the synthesis of a biotinylated doxorubicin analogue that retains topoisomerase activity.

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Section: Discussionmentioning

confidence: 99%

A Stable Bis-Allyloxycarbonyl Biotin Aldehyde Derivative for Biotinylation via Reductive Alkylation: Application to the Synthesis of a Biotinylated Doxorubicin Derivative

et al. 2002

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“…To test the reaction in the presence of fragile biomolecules, an excess (500 wt %) of the enzyme RNAase‐A was added, which remained unaltered after complete reaction as evidenced by capillary electrophoresis. On the basis of these model experiments, 4‐iodobenzoate was coupled to ω‐tetradecynoic acid, a long‐chain terminal alkynyl fatty acid;96a the amount of palladium was increased to 10 mol %, because of decomposition of the catalytic system (formation of palladium black), to quantitatively functionalize the alkynyl lipid within 15 minutes.…”

Section: Sonogashira–heck Alkynylations In the Homogeneous Phasementioning

confidence: 99%

Palladium‐Based Catalytic Systems for the Synthesis of Conjugated Enynes by Sonogashira Reactions and Related Alkynylations

2007

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Conjugated alkynes are recurring building blocks in natural products, a wide range of industrial intermediates, pharmaceuticals and agrochemicals, and molecular materials for optics and electronics. The palladium-catalyzed cross-coupling between sp(2)-hybridized carbon atoms of aryl, heteroaryl, and vinyl halides with sp-hybridized carbon atoms of terminal acetylenes is one of the most important developments in the field of alkyne chemistry over the past 50 years. The seminal work of the 1970s has initiated an intense search for more general and reliable reaction conditions. The interest in the catalytic activation of demanding substrates, the need to minimize the consumption of depletive resources, and the search for easy access to an increased variety of functionalized enynes has led to the current generations of high-turnover catalysts. This Review gives an overview of the highly efficient palladium catalyst systems for the direct alkynylation of C(sp(2)) halides with terminal alkynes, both in homogeneous and heterogeneous phases.

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“…Mauduit and co-workers reported (271) the synthesis of an alkyl imidazolium salt supported ruthenium catalyst A ( Table 3). The catalyst was used in RCM of N,N-diallyltosylamide (136) with low reactivity such as 2-naphthaldehyde or p-anisaldehyde. Interestingly, in the IL, the electrondeficient aldehydes showed the highest activity which is the opposite trend to that found in molecular solvents, including water.…”

Section: Ring-closing Metathesis (Rcm) Of Dienesmentioning

confidence: 99%

Selective chemical reactions in supercritical carbon dioxide, water, and ionic liquids

Skouta

2009

Green Chemistry Letters and Reviews

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Sonogashira cross-couplings using biocompatible conditions in water

Cited by 60 publications

References 13 publications

A Stable Bis-Allyloxycarbonyl Biotin Aldehyde Derivative for Biotinylation via Reductive Alkylation: Application to the Synthesis of a Biotinylated Doxorubicin Derivative

A Stable Bis-Allyloxycarbonyl Biotin Aldehyde Derivative for Biotinylation via Reductive Alkylation: Application to the Synthesis of a Biotinylated Doxorubicin Derivative

Palladium‐Based Catalytic Systems for the Synthesis of Conjugated Enynes by Sonogashira Reactions and Related Alkynylations

Selective chemical reactions in supercritical carbon dioxide, water, and ionic liquids

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