Wahre Spurlosigkeit: eine Nomenklatur für Linker

Comely, Alex C.

doi:10.1002/1521-3757(20010316)113:6<1042::aid-ange10420>3.0.co;2-z

Angew. Chem.

2001

DOI: 10.1002/1521-3757(20010316)113:6<1042::aid-ange10420>3.0.co;2-z

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Wahre Spurlosigkeit: eine Nomenklatur für Linker

Alex C. Comely

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Cited by 5 publications

References 324 publications

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An Engineered Linker Capable of Promoting On‐Resin Reactions for Microwave‐Assisted Solid‐Phase Organic Synthesis

Sun

Dai

2006

Angewandte Chemie

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Ein aktiver Link: Der Diglycin enthaltende Linker (Kat.⋅Linker) auf einem Rink‐Amid‐Harz sollte zwei Funktionen übernehmen: a) die Anbindung eines Gerüsts und b) das Einfangen von Metallionen, um Reaktionen auf dem Harz zu unterstützen (siehe Bild). Die Fähigkeit des Linkers, Metallionen zu binden, erwies sich als wesentlich für die Festphasensynthese von Indolen durch CuII‐vermittelte Heteroanellierung unter Mikrowellenbestrahlung.

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An Engineered Linker Capable of Promoting On‐Resin Reactions for Microwave‐Assisted Solid‐Phase Organic Synthesis

Sun

Dai

2006

Angewandte Chemie

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An Engineered Linker Capable of Promoting On‐Resin Reactions for Microwave‐Assisted Solid‐Phase Organic Synthesis

Sun

Dai

2006

Angew Chem Int Ed

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Development of the Traceless Phenylhydrazide Linker for Solid‐Phase Synthesis

Stieber¹,

Grether²,

Waldmann³

2003

Chemistry A European J

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The hydrazide group is a new oxidatively cleavable traceless linker for solid-phase chemistry. It can be readily introduced by hydrazide formation between a carboxy-functionalized resin and different substituted hydrazines. In order to achieve high yields in this step, new carboxylic acid resins were developed that are not prone to undesired imide formation upon activation of the carboxylic acid. The polymer-bound acyl hydrazides were successfully employed in various transformations, namely Heck, Suzuki, Sonogashira, and Stille couplings, as well as Wittig and Grignard reactions. Traceless release of the coupling products from the solid support is achieved selectively under mild conditions and in high purity by oxidation of the aryl hydrazides to acyl diazenes with Cu(II) salts or N-bromosuccinimide (NBS) and subsequent nucleophilic attack of the acyl diazene intermediates. Traceless cleavage by oxidation with NBS can be carried out as a two-step process in which stable acyl diazenes are first generated by treatment with NBS in the absence of a nucleophile. After removal of the reagents by simple resin washing, the traceless release is effected by the addition of methanol, which leads to products of high purity without any additional separation steps.

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Wahre Spurlosigkeit: eine Nomenklatur für Linker

Cited by 5 publications

References 324 publications

An Engineered Linker Capable of Promoting On‐Resin Reactions for Microwave‐Assisted Solid‐Phase Organic Synthesis

An Engineered Linker Capable of Promoting On‐Resin Reactions for Microwave‐Assisted Solid‐Phase Organic Synthesis

An Engineered Linker Capable of Promoting On‐Resin Reactions for Microwave‐Assisted Solid‐Phase Organic Synthesis

Development of the Traceless Phenylhydrazide Linker for Solid‐Phase Synthesis

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