Alkyl Halide-Free Heteroatom Alkylation and Epoxidation Facilitated by a Recyclable Polymer-Supported Oxidant for the In-Flow Preparation of Diazo Compounds

Highly reactive metal carbenes, generated from simple ketones via diazo compounds, including diazo‐amides and ‐phosphonates, using a recyclable reagent in‐flow, are transient but versatile electrophiles for heteroatom alkylation reactions and for epoxide formation. The method produces no organic was...

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Veröffentlicht in:Chemistry : a European journal 2015-03, Vol.21 (12), p.4576-4579
Hauptverfasser: Nicolle, Simon M., Hayes, Christopher J., Moody, Christopher J.
Format: Artikel
Sprache:eng
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Zusammenfassung:Highly reactive metal carbenes, generated from simple ketones via diazo compounds, including diazo‐amides and ‐phosphonates, using a recyclable reagent in‐flow, are transient but versatile electrophiles for heteroatom alkylation reactions and for epoxide formation. The method produces no organic waste, with the only by‐products being water, KI and nitrogen, without the attendant hazards of isolation of intermediate diazo compounds. Highly reactive metal carbenes, generated from simple ketones via diazo compounds, using a recyclable reagent in‐flow, are transient but versatile electrophiles for heteroatom alkylation reactions and for epoxide formation (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201500118