title: Alkyl halide-free heteroatom alkylation and epoxidation facilitated by a recyclable polymer-supported oxidant for the in-flow preparation of diazo compounds.
abstract: 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.
authors: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD (UK).
authors: Simon M
authors: SM
authors: Nicolle
authors: Christopher J
authors: CJ
authors: Hayes
authors: Christopher J
authors: CJ
authors: Moody
mesh_terms: D000478:Alkylation; D000577:Amides / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry; D006219:Halogens / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D016877:Oxidants / Q000737:chemistry*; D010757:Phosphorous Acids / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*
chemical_list: D000577:Amides; D001391:Azo Compounds; D004852:Epoxy Compounds; D006219:Halogens; D007659:Ketones; D016877:Oxidants; D010757:Phosphorous Acids; D011108:Polymers; C570063:phosphonic acid
keywords: alkylation; carbenes; epoxidation; oxidation; recyclable supported reagents