Polymer-bound diazonium salts for the synthesis of diazoacetic esters

Schroen, Maarten; Bräse, Stefan

doi:10.1016/j.tet.2005.09.145

Cited by 19 publications

(19 citation statements)

References 40 publications

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“…Common methods include (i) diazo transfer, 58,59 (ii) diazotization, 60,61 (iii) hydrazone decomposition 62,63 or hydrazone oxidation, 64,65 (iv) rearrangement of N -alkyl N -nitroso compounds, 8,66 (v) 1,3-disubstituted acyl (or aryl) triazine fragmentation, 67,68 and (vi) elaboration of other diazo compounds (Figure 2). 69–73 Most of these routes have been reviewed extensively for their merits in the context of synthetic chemistry.…”

Section: Preparationmentioning

confidence: 99%

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Diazo Compounds: Versatile Tools for Chemical Biology

2016

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Diazo groups have broad and tunable reactivity. That and other attributes endow diazo compounds with the potential to be valuable reagents for chemical biologists. The presence of diazo groups in natural products underscores their metabolic stability and anticipates their utility in a biological context. The chemoselectivity of diazo groups, even in the presence of azido groups, presents many opportunities. Already, diazo compounds have served as chemical probes and elicited novel modifications of proteins and nucleic acids. Here, we review advances that have facilitated the chemical synthesis of diazo compounds, and we highlight applications of diazo compounds in the detection and modification of biomolecules.

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Section: Preparationmentioning

confidence: 99%

“…The ensuing triazenophosphonium intermediate hydrolyzes quickly in water to form an acyl triazene, which is a known precursor to a diazo group. 67,68 …”

Section: Preparationmentioning

confidence: 99%

Diazo Compounds: Versatile Tools for Chemical Biology

2016

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“…Die Methode eignet sich auch, um a-Bromketone in a-Diazoketone umzuwandeln, wie am Beispiel von 2-Diazo-1-phenyl-1-ethanon (w-Diazoacetophenon) gezeigt wurde. [42] oder einer Base [43] die Fragmentierung zu einem a-Diazocarbonsäureester und einem aromatischen Amin ein (Schema 9). Wegen der begrenzten Anwendungsbreite und der mäßigen Ausbeuten hat diese Methode allerdings bisher keine präpa-rative Bedeutung erlangt.…”

Section: Diazoverbindungen Aus Hydrazonenunclassified

Neues zur Synthese von Diazoverbindungen

Maas

2009

Angewandte Chemie

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Aufgrund der vielseitigen und nützlichen Folgechemie von Diazoverbindungen (R1R2CN2) ist das Interesse an dieser Substanzklasse seit Jahren ungebrochen. Dabei wird auch das bereits vorhandene Methodenrepertoire zur Herstellung von Diazoverbindungen immer wieder um neue Verfahren oder um neuartige Varianten etablierter Synthesewege ergänzt. Nicht selten tragen die neuen Synthesevorschläge der Labilität und beachtlichen chemischen Reaktivität bestimmter Typen von Diazoverbindungen Rechnung, aber auch dem Aspekt umweltfreundlicherer Methodik wurde Beachtung geschenkt.

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“…The electron distribution in acyl triazenes is similar to that in the triazenes employed by Baumgarten,and Schroen and Bräse ([Eqs. (1) and (2)] [10] ), and we suspected that such triazenes would be competent precursors of diazo compounds.…”

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confidence: 99%

“…Depending upon their stability and coexisting functional groups, diazo compounds can present a challenge with respect to their preparation and isolation. Current methods include a) diazo transfer, [5] b) diazotization, [6] c) decomposition [7] or oxidation [8] of hydrazones, d) rearrangement of N-alkyl N-nitroso compounds, [9] e) fragmentation of 1,3-disubstituted alkyl aryl triazenes, [10] and f) elaboration of more readily available diazo compounds (Scheme 1). [11] The preparation of diazo compounds via the fragmentation of triazenes is uncommon.…”

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confidence: 99%