Vinylphosphonium and 2-aminovinylphosphonium salts – preparation and applications in organic synthesis
- Anna Kuźnik,
- Roman Mazurkiewicz and
- Beata Fryczkowska
Beilstein J. Org. Chem. 2017, 13, 2710–2738, doi:10.3762/bjoc.13.269
Graphical Abstract
Scheme 1: Generation of phosphorus ylides from vinylphosphonium salts.
Scheme 2: Intramolecular Wittig reaction with the use of vinylphosphonium salts.
Scheme 3: Alkylation of diphenylvinylphosphine with methyl or benzyl iodide.
Scheme 4: Methylation of isopropenyldiphenylphosphine with methyl iodide.
Scheme 5: Alkylation of phosphines with allyl halide derivatives and subsequent isomerization of intermediate...
Scheme 6: Alkylation of triphenylphosphine with vinyl triflates in the presence of (Ph3P)4Pd.
Scheme 7: Mechanism of alkylation of triphenylphosphine with vinyl triflates in the presence of (Ph3P)4Pd as ...
Scheme 8: β-Elimination of phenol from β-phenoxyethyltriphenylphosphonium bromide.
Scheme 9: β-Elimination of phenol from β-phenoxyethylphosphonium salts in an alkaline environment.
Scheme 10: Synthesis and subsequent dehydrohalogenation of α-bromoethylphosphonium bromide.
Scheme 11: Synthesis of tributylvinylphosphonium iodides via Peterson-type olefination of α-trimethylsilylphos...
Scheme 12: Synthesis of 1-cycloalkenetriphenylphosphonium salts by electrochemical oxidation of triphenylphosp...
Scheme 13: Suggested mechanism for the electrochemical synthesis of 1-cycloalkenetriphenylphosphonium salts.
Scheme 14: Generation of α,β-(dialkoxycarbonyl)vinylphosphonium salts by addition of triphenylphosphine to ace...
Scheme 15: Synthesis of 2-(N-acylamino)vinylphosphonium halides by imidoylation of β-carbonyl ylides with imid...
Scheme 16: Imidoylation of β-carbonyl ylides with imidoyl halides generated in situ.
Scheme 17: Synthesis of 2-benzoyloxyvinylphosphonium bromide from 2-propynyltriphenylphosphonium bromide.
Scheme 18: Synthesis of 2-aminovinylphosphonium salts via nucleophilic addition of amines to 2-propynyltriphen...
Scheme 19: Deacylation of 2-(N-acylamino)vinylphosphonium chlorides to 2-aminovinylphosphonium salts.
Scheme 20: Resonance structures of 2-aminovinylphosphonium salts and tautomeric equilibrium between aminovinyl...
Scheme 21: Synthesis of 2-aminovinylphosphonium salts by reaction of (formylmethyl)triphenylphosphonium chlori...
Scheme 22: Generation of ylides by reaction of vinyltriphenylphosphonium bromide with nucleophiles and their s...
Scheme 23: Intermolecular Wittig reaction with the use of vinylphosphonium bromide and organocopper compounds ...
Scheme 24: Intermolecular Wittig reaction with the use of ylides generated from vinylphosphonium bromides and ...
Scheme 25: Direct transformation of vinylphosphonium salts into ylides in the presence of potassium tert-butox...
Scheme 26: A general method for synthesis of carbo- and heterocyclic systems by the intramolecular Wittig reac...
Scheme 27: Synthesis of 2H-chromene by reaction of vinyltriphenylphosphonium bromide with sodium 2-formylpheno...
Scheme 28: Synthesis of 2,5-dihydro-2,3-dimethylfuran by reaction of vinylphosphonium bromide with 3-hydroxy-2...
Scheme 29: Synthesis of 2H-chromene and 2,5-dihydrofuran derivatives in the intramolecular Wittig reaction wit...
Scheme 30: Enantioselective synthesis of 3,6-dihydropyran derivatives from vinylphosphonium bromide and enanti...
Scheme 31: Synthesis of 2,5-dihydrothiophene derivatives in the intramolecular Wittig reaction from vinylphosp...
Scheme 32: Synthesis of bicyclic pyrrole derivatives in the reaction of vinylphosphonium halides and 2-pyrrolo...
Scheme 33: Stereoselective synthesis of bicyclic 2-pyrrolidinone derivatives in the reaction of vinylphosphoni...
Scheme 34: Stereoselective synthesis of 3-pyrroline derivatives in the intramolecular Wittig reaction from vin...
Scheme 35: Synthesis of cyclic alkenes in the intramolecular Wittig reaction from vinylphosphonium bromide and...
Scheme 36: Synthesis of 1,3-cyclohexadienes by reaction of 1,3-butadienyltriphenylphosphonium bromide with eno...
Scheme 37: Synthesis of bicyclo[3.3.0]octenes by reaction of vinylphosphonium salts with cyclic diketoester.
Scheme 38: Synthesis of quinoline derivatives in the intramolecular Wittig reaction from 2-(2-acylphenylamino)...
Scheme 39: Stereoselective synthesis of γ-aminobutyric acid in the intermolecular Wittig reaction from chiral ...
Scheme 40: Synthesis of allylamines in the intermolecular Wittig reaction from 2-aminovinylphosphonium bromide...
Scheme 41: A general route towards α,β-di(alkoxycarbonyl)vinylphosphonium salts and their subsequent possible ...
Scheme 42: Generation of resonance-stabilized phosphorus ylides via the reaction of triphenylphosphine with di...
Scheme 43: Synthesis of resonance-stabilized phosphorus ylides in the reaction of triphenylphosphine, dialkyl ...
Scheme 44: Synthesis of resonance-stabilized phosphorus ylides via the reaction of triphenylphosphine with dia...
Scheme 45: Generation of resonance-stabilized phosphorus ylides in the reaction of acetylenedicarboxylate, tri...
Scheme 46: Synthesis of resonance-stabilized phosphorus ylides via the reaction of dialkyl acetylenedicarboxyl...
Scheme 47: Synthesis of resonance-stabilized ylides derived from semicarbazones, aromatic amides, and 3-(aryls...
Scheme 48: Synthesis of resonance-stabilized ylides via the reaction of triphenylphosphine with dialkyl acetyl...
Scheme 49: Synthesis of resonance-stabilized ylides in the reaction of triphenylphosphine, dialkyl acetylenedi...
Scheme 50: Synthesis of N-acylated α,β-unsaturated γ-lactams via resonance-stabilized phosphorus ylides derive...
Scheme 51: Synthesis of resonance-stabilized phosphorus ylides derived from 6-amino-N,N'-dimethyluracil and th...
Scheme 52: Generation of resonance-stabilized phosphorus ylides in the reaction of triphenylphosphine, dialkyl...
Scheme 53: Synthesis of resonance-stabilized phosphorus ylides via the reaction of triphenylphosphine with dia...
Scheme 54: Synthesis of 1,3-dienes via intramolecular Wittig reaction with the use of resonance-stabilized yli...
Scheme 55: Synthesis of 1,3-dienes in the intramolecular Wittig reaction from ylides generated from dimethyl a...
Scheme 56: Synthesis of 4-(2-quinolyl)cyclobutene-1,2,3-tricarboxylic acid triesters and isomeric cyclopenteno...
Scheme 57: Synthesis of 4-arylquinolines via resonance-stabilized ylides in the intramolecular Wittig reaction....
Scheme 58: Synthesis of furan derivatives via resonance-stabilized ylides in the intramolecular Wittig reactio...
Scheme 59: Synthesis of 1,3-indanedione derivatives via resonance-stabilized ylides in the intermolecular Witt...
Scheme 60: Synthesis of coumarin derivatives via nucleophilic displacement of the triphenylphosphonium group i...
Scheme 61: Synthesis of 6-formylcoumarin derivatives and their application in the synthesis of dyads.
Scheme 62: Synthesis of di- and tricyclic coumarin derivatives in the reaction of pyrocatechol with two vinylp...
Scheme 63: Synthesis of mono-, di-, and tricyclic derivatives in the reaction of pyrogallol with one or two vi...
Scheme 64: Synthesis of 1,4-benzoxazine derivative by nucleophilic displacement of the triphenylphosphonium gr...
Scheme 65: Synthesis of 7-oxo-7H-pyrido[1,2,3-cd]perimidine derivative via nucleophilic displacement of the tr...
Scheme 66: Application of vinylphosphonium salts in the Diels–Alder reaction with dienes.
Scheme 67: Synthesis of pyrroline derivatives from vinylphosphonium bromide and 5-(4H)-oxazolones.
Scheme 68: Synthesis of pyrrole derivatives in the reactions of vinyltriphenylphosphonium bromide with protona...
Scheme 69: Synthesis of dialkyl 2-(alkylamino)-5-aryl-3,4-furanedicarboxylates via intermediate α,β-di(alkoxyc...
Scheme 70: Synthesis of 1,4-benzoxazine derivatives from acetylenedicarboxylates, phosphines, and 1-nitroso-2-...
1-Imidoalkylphosphonium salts with modulated Cα–P+ bond strength: synthesis and application as new active α-imidoalkylating agents
- Jakub Adamek,
- Roman Mazurkiewicz,
- Anna Węgrzyk and
- Karol Erfurt
Beilstein J. Org. Chem. 2017, 13, 1446–1455, doi:10.3762/bjoc.13.142
Graphical Abstract
Scheme 1: α-Amidoalkylation reactions under basic or acidic conditions.
Scheme 2: Synthetic routes of α-amido- and α-imidoalkylation of aromatic and heteroaromatic compounds.
Scheme 3: Reaction of imidophosphonium salt 5e with 1,3,5-trimethoxybenzene.
A new method for the synthesis of α-aminoalkylidenebisphosphonates and their asymmetric phosphonyl-phosphinyl and phosphonyl-phosphinoyl analogues
- Anna Kuźnik,
- Roman Mazurkiewicz,
- Mirosława Grymel,
- Katarzyna Zielińska,
- Jakub Adamek,
- Ewa Chmielewska,
- Marta Bochno and
- Sonia Kubica
Beilstein J. Org. Chem. 2015, 11, 1418–1424, doi:10.3762/bjoc.11.153
Graphical Abstract
Figure 1: General structure of bisphosphonates.
Figure 2: General structures of 1-hydroxy- and 1-amino-1-phosphinylalkylphosphonates (2 and 3, respectively) ...
Scheme 1: Electrochemical α-methoxylation of 1-(N-acylamino)alkylphosphonates.
Scheme 2: Transformation of diethyl 1-(N-acetylamino)-1-methoxyalkylphosphonates into bisphosphoric acid este...
