134166-48-6Relevant academic research and scientific papers
An Enzymatic Platform for Primary Amination of 1-Aryl-2-alkyl Alkynes
Liu, Zhen,Qin, Zi-Yang,Zhu, Ledong,Athavale, Soumitra V.,Sengupta, Arkajyoti,Jia, Zhi-Jun,Garcia-Borràs, Marc,Houk,Arnold, Frances H.
supporting information, p. 80 - 85 (2022/01/08)
Propargyl amines are versatile synthetic intermediates with numerous applications in the pharmaceutical industry. An attractive strategy for efficient preparation of these compounds is nitrene propargylic C(sp3)-H insertion. However, achieving this reacti
Benzene-1,3,5-triyl Triformate (TFBen)-Promoted Palladium-Catalyzed Carbonylative Synthesis of 2-Oxo-2,5-dihydropyrroles from Propargyl Amines
Ying, Jun,Le, Zhengjie,Wu, Xiao-Feng
, p. 194 - 198 (2020/01/03)
In this letter, we developed a palladium-catalyzed procedure for the cyclocarbonylation of propargyl amines. Benzene-1,3,5-triyl triformate (TFBen) has been explored as the CO source and also as the key promotor. Various substituted 2-oxo-dihydropyrroles were produced in a facile manner in good yields (up to 90%).
Synthesis of Spirobicyclic Pyrazoles by Intramolecular Dipolar Cycloadditions/[1s, 5s] Sigmatropic Rearrangements
Dimirjian, Christine A.,Casti?eira Reis, Marta,Balmond, Edward I.,Turman, Nolan C.,Rodriguez, Elys P.,Di Maso, Michael J.,Fettinger, James C.,Tantillo, Dean J.,Shaw, Jared T.
, p. 7209 - 7212 (2019/10/02)
The formation of fused pyrazoles via intramolecular 1,3-dipolar cycloadditions of diazo intermediates with pendant alkynes is described. A subsequent thermal [1s, 5s] sigmatropic shift of these pyrazole systems resulted in a ring contraction, forming spirocyclic pyrazoles. The limitations of this rearrangement were explored by changing the substituents on the nonmigrating aromatic ring and by using substrates lacking an aromatic linkage to the propargyl group.
On the Distribution of Linear versus Angular Naphthalenes in Aromatic Tetradehydro-Diels–Alder Reactions – Effect of Linker Structure and Steric Bulk
Chinta, Bhavani Shankar,Baire, Beeraiah
supporting information, p. 3381 - 3385 (2017/06/29)
We report here a systematic study of the aromatic tetradehydro-Diels–Alder (Ar-TDDA) reaction to elucidate the factors that have significant effects on the distribution of linear and angular naphthalene products. Two factors were studied, that is, the nat
Palladium(II)-Catalyzed Directed anti-Hydrochlorination of Unactivated Alkynes with HCl
Derosa, Joseph,Cantu, Annabelle L.,Boulous, Mark N.,O'Duill, Miriam L.,Turnbull, Joshua L.,Liu, Zhen,De La Torre, Daizy M.,Engle, Keary M.
, p. 5183 - 5193 (2017/05/04)
A regioselective anti-hydrochlorination of unactivated alkynes is reported. The reaction utilizes in situ generated HCl as the source of both the Cl- and H+ and is catalyzed by palladium(II) acetate, with loadings as low as 25 ppm. Removable picolinamide and 8-aminoquinoline bidentate directing groups are used to control the regioselectivity of the chloropalladation step and stabilize the resulting alkenylpalladium(II) intermediate for subsequent protodepalladation. This method provides access to a broad array of substituted alkenyl chlorides in excellent yields and with high regioselectivity. The products from this transformation were successfully derivatized via Stille coupling to a variety of trisubstituted alkene products. Reaction progress kinetic analysis was performed, shedding light on a possible mechanism for this catalytic process.
Non-enzymatic acylative kinetic resolution of primary allylic amines
Kolleth, Amandine,Cattoen, Martin,Arseniyadis, Stellios,Cossy, Janine
, p. 9338 - 9340 (2013/10/01)
A non-enzymatic acetyl transfer-based kinetic resolution of primary allylic amines is reported. The process involves the use of (1S,2S)-1 in conjunction with a supported ammonium salt and affords the corresponding enantio-enriched N-acetylated allylic ami
Rhodium-Catalysed Reactions of Propargylamines with CO/H2. Formation of Pyrroles and Butenolides
Campi, Eva M.,Fallon, Gary D.,Jackson, W. Roy,Nilsson, Ylva
, p. 1167 - 1178 (2007/10/02)
Rhodium-catalysed reactions of (arylpropargyl)amines with CO/H2 give β-arylpyrroles in good yields.Reactions of (alkylpropargyl)amines gave alkylpyrroles together with butenolides which are formed in an unusual reaction that probably involves double carbonylation, reduction of one carbonyl function and removal of the amine function by hydrogenolysis.The single-crystal X-ray structure of 5-methyl-N,3-diphenylpyrrole-2-carboxamide is recorded.
