147722-49-4Relevant articles and documents
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
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.
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.
