81374-48-3

Upstream product

• 109-97-7 pyrrole 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 103-64-0 bromostyrene 
• 536-74-3 phenylacetylene 
• 637-44-5 phenylpropyolic acid 
• 4110-77-4 (E)-β-chlorostyrene 
• 51297-15-5 α-Pyrrolomethanphosphonsaeurediethylester 
• 13401-81-5 1-vinyl-1H-pyrrole 
• 591-50-4 iodobenzene 
• 345291-01-2 (2-Hydroxy-2-phenyl-1-pyrrol-1-yl-ethyl)-phosphonic acid diethyl ester 

Relevant academic research and scientific papers

Inorganic base-mediated stereoselective hydroamination of arylalkynes with imidazole: An efficient access to N-vinylimidazoles

A metal-free inorganic base-mediated highly stereoselective hydroamination of arylalkynes with imidazoles has been developed, and the corresponding N-vinylimidazoles were obtained in good yields and with moderate to excellent stereoselectivities (up to 99

Decarboxylative Hydroamination of 3-Arylpropiolic Acids with N-Heterocycles under Transition-Metal-Free Conditions

A decarboxylative hydroamination cascade reaction of 3-arylpropiolic acids with N-heterocycles under transition-metal-free conditions was developed. 3-Arylpropiolic acids were found to react smoothly with a range of N-heterocycles under the effect of t-BuOK to afford N-vinyl heterocycles in moderate to excellent yields. This reaction represents the first decarboxylative hydroamination of 3-arylpropiolic acids without the aid of a transition-metal catalyst. Georg Thieme Verlag Stuttgart, New York.

Expedient one-step synthesis of nitrogen stilbene analogs by transition metal-free hydroamination of arylacetylenes with pyrroles

A novel family of nitrogen stilbene analogs, 1-styrylpyrroles, has been synthesized in good to excellent yields by a straightforward facile transition metal-free addition of pyrroles to arylacetylenes in the KOH/DMSO system (90-120 °C, 5-13 h). Thermodynamically controlled E/Z-isomer ratio of 1-styrylpyrroles depends on structure of both pyrroles and acetylenes ranging from ca. 100% E-stereoselectivity (for the pair unsubstituted pyrrole - phenylacetylene) to 90, 96% Z-stereoselectivity (for the pairs: 2-phenylpyrrole - phenylacetylene and 2-(2-thienyl)pyrrole - phenylacetylene, respectively).

CuI-catalyzed cross-coupling reaction of (E)-vinyl bromides with nitrogen-containing heterocycles

An efficient and straightforward copper-catalyzed method allowing vinylation of N-nucleophiles with various substituted (E)-vinyl bromides under palladium-free and ligand-free conditions has taken a high yield (up to 95%). Noteworthy is that the doublebond geometry of these vinyl halides was retained with our protocol.

Mild copper-catalyzed vinylation reactions of azoles and phenols with vinyl bromides

An efficient and straightforward copper-catalyzed method allowing vinylation of N- or O-nucleophiles with di- or trisubstituted vinyl bromides is reported. The procedure is applicable to a broad range of substrates since N-vinylation of mono-, di-, and tr

Palladium-catalyzed stereocontrolled vinylation of azoles and phenothiazine

(formula presented) Vinylation of various azoles (pyrrole, indole, carbazole, and their derivatives) and phenothiazine with vinyl bromides catalyzed by palladium-phosphine complexes results in the respective N-vinylazoles in 30-99% yields. This reaction w

Regioselective α-Arylation of N-Vinylpyrroles by the Heck Reaction

A number of N-vinylpyrroles were arylated for the first time with aryl iodides in the presence of palladium compounds. N-Vinylpyrroles are thus smoothly converted into the corresponding N-arylethenyl derivatives. The regioselectivity of substitution at th

α-Substituted Phosphonates. 37. Derivatives of α-Pyrrolomethanephosphonic Acid and N-Vinylpyrroles

Diethyl α-aminomethanephosphonate 5a and its α-aryl derivatives 5b-d react with 2,5-diethoxytetrahydrofuran 1 to give diethyl α-pyrrolomethanephosphonate 9a and the α-aryl derivatives 9b-d, respectively.The pyrrolo derivatives 9 can be converted into the lithium salts 15 and 16, respectively, which with carbonyl compounds undergo the Horner reaction yielding E/Z mixtures of N-vinylpyrroles 18.In certain cases the intermediate of the Horner reaction, the β-hydroxyphosphonate, 17 can be isolated.The pyrrolo-analogue of stilbene, 18a, is formed only as E-isomer.On treating the lithium salts 15 and 16 with 9 or with alkyl halides α-C-alkylated pyrrolophosphonates 22 and 23, respectively, are obtained.