title: Methyltriphenylphosphonium Methylcarbonate, an All-In-One Wittig Vinylation Reagent.
abstract: The methyltriphenylphosphonium methylcarbonate salt [Ph3 PCH3 ][CH3 OCO2 ], obtained directly by quaternarization of triphenylphosphine with dimethylcarbonate, is a latent ylide that promotes Wittig vinylation of aldehydes and ketones. Alkenes are obtained simply by mixing [Ph3 PCH3 ][CH3 OCO2 ] and the carbonyl and heating in a solvent (no base, no halides, and no inorganic byproducts). Deuterium exchange experiments and the particularly short anion-cation distance measured by XRD in [Ph3 PCH3 ][CH3 OCO2 ] allowed to explain the nature and reactivity of this species. Green chemistry metrics (atom economy, mass index, environmental factor) indicate that this vinylation procedure is more efficient than comparable ones. Deuterated [Ph3 PCD3 ][CH3 OCO2 ] promoted the synthesis of deuterated olefins.
authors.affiliation: Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca' Foscari Venezia, Dorsoduro 2137, 30123, Venezia, Italy.
authors.forename: Lisa
authors.identifier: http://orcid.org/0000-0002-3217-422X
authors.initials: L
authors.lastname: Cattelan
authors.affiliation: Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca' Foscari Venezia, Dorsoduro 2137, 30123, Venezia, Italy.
authors.forename: Marco
authors.identifier: http://orcid.org/0000-0003-2969-6227
authors.initials: M
authors.lastname: Noè
authors.affiliation: Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca' Foscari Venezia, Dorsoduro 2137, 30123, Venezia, Italy.
authors.forename: Maurizio
authors.initials: M
authors.lastname: Selva
authors.affiliation: Elettra-Sincrotrone Trieste, S.S. 14 Km 163.5 in Area, Science Park, 34149, Basovizza-Trieste, Italy.
authors.forename: Nicola
authors.initials: N
authors.lastname: Demitri
authors.affiliation: Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca' Foscari Venezia, Dorsoduro 2137, 30123, Venezia, Italy. alvise@unive.it.
authors.forename: Alvise
authors.identifier: http://orcid.org/0000-0003-4544-8709
authors.initials: A
authors.lastname: Perosa
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D009861:Onium Compounds / Q000737:chemistry*; D014320:Triphenylmethyl Compounds / Q000737:chemistry*
chemical_list: D000475:Alkenes; D007202:Indicators and Reagents; D009861:Onium Compounds; D014320:Triphenylmethyl Compounds; C011561:triphenylmethylphosphonium
keywords: Wittig reactions; green chemistry; halides; phosphorus; ylides