1719-19-3Relevant articles and documents
Sonogashira-Hagihara and Buchwald-Hartwig cross-coupling reactions with sydnone and sydnone imine derived catalysts
Lücke, Ana-Luiza,Pruschinski, Lucas,Freese, Tyll,Schmidt, Andreas
, p. 94 - 104 (2018)
Seven different palladium complexes of sydnones and sydnone imines and a co-catalyst system consisting of lithium sydnone-4-carboxylate and Pd(PPh3)4 catalyzed Sonogashira-Hagihara reactions between (hetero)- aromatic bromides and 2-methylbut-3-yn-2-ol (52 examples, up to 100% yield). The co-catalyst system and a sydnone Pd complex were also tested in Buchwald-Hartwig reactions (9 examples, up to 100% yield). (Equation Presented).
Palladium(II)-Catalyzed Reaction of Lawsones and Propargyl Carbonates: Construction of 2,3-Furanonaphthoquinones and Evaluation as Potential Indoleamine 2,3-Dioxygenase Inhibitors
Feng, Xi,Qiu, Xiaqiu,Huang, Huidan,Wang, Jubo,Xu, Xi,Xu, Pengfei,Ge, Ruijia,Liu, Xiaojin,Li, Zhiyu,Bian, Jinlei
, p. 8003 - 8010 (2018)
An efficient reaction utilizing propargyl carbonates through Claisen rearrangement to synthesize furanonaphthoquinones is described. The remarkable transformation exhibits excellent functional group tolerance, affording the target furanonaphthoquinones in
Klein,Aminadav
, p. 1380 (1970)
Hollow palladium-cobalt bimetallic nanospheres as an efficient and reusable catalyst for Sonogashira-type reactions
Li, Hui,Zhu, Zhonghong,Liu, Jun,Xie, Songhai,Li, Hexing
, p. 4366 - 4370 (2010)
The synthesis and characterization of hollow Pd-Co bimetallic nanospheres are reported. During Sonogashira-type coupling reactions between aryl halides and terminal alkynes in aqueous medium, these hollow materials exhibited much higher activity than the solid counterpart nanoparticles. Moreover, the catalytic activity could be adjusted via changing the catalyst composition. The enhanced activity was attributed to both the hollow chamber structure and the promotional effect of Co-dopants, which provided more Pd active sites for the reactants. The Royal Society of Chemistry 2010.
Alcohol Dehydrogenases and N-Heterocyclic Carbene Gold(I) Catalysts: Design of a Chemoenzymatic Cascade towards Optically Active β,β-Disubstituted Allylic Alcohols
González-Granda, Sergio,Lavandera, Iván,Gotor-Fernández, Vicente
supporting information, p. 13945 - 13951 (2021/04/22)
The combination of gold(I) and enzyme catalysis is used in a two-step approach, including Meyer–Schuster rearrangement of a series of readily available propargylic alcohols followed by stereoselective bioreduction of the corresponding allylic ketone intermediates, to provide optically pure β,β-disubstituted allylic alcohols. This cascade involves a gold N-heterocyclic carbene and an enzyme, demonstrating the compatibility of both catalyst types in aqueous medium under mild reaction conditions. The combination of [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene][bis(trifluoromethanesulfonyl)-imide]gold(I) (IPrAuNTf2) and a selective alcohol dehydrogenase (ADH-A from Rhodococcus ruber, KRED-P1-A12 or KRED-P3-G09) led to the synthesis of a series of optically active (E)-4-arylpent-3-en-2-ols in good yields (65–86 %). The approach was also extended to various 2-hetarylpent-3-yn-2-ol, hexynol, and butynol derivatives. The use of alcohol dehydrogenases of opposite selectivity led to the production of both allyl alcohol enantiomers (93->99 % ee) for a broad panel of substrates.
Ru(ii)-catalyzed allenylation and sequential annulation of: N -tosylbenzamides with propargyl alcohols
Kumar, Shreemoyee,Nair, Akshay M.,Volla, Chandra M. R.
supporting information, p. 6280 - 6283 (2021/07/02)
We hereby report Ru(ii)-catalyzed C(sp2)-H allenylation of N-tosylbenzamides to access multi-substituted allenylamides. Furthermore, the allenylamides were converted to the corresponding isoquinolone derivatives via base mediated annulation. The current protocol features low catalyst loading, mild reaction conditions, high functional group compatibility and desired scalability. The unique functionality of the afforded allenes allowed further transformations to expand the practicality of the protocol. This journal is
Rhodium-catalyzed oxidative coupling of benzoic acids with propargyl alcohols: An efficient access to isocoumarins
Luo, Feihua,He, Shuhua,Gou, Quan,Chen, Jinyang,Zhang, mingzhong
supporting information, (2020/12/29)
An efficient protocol of Rh(III)-catalyzed oxidative cyclization of benzoic acids with propargyl alcohols to give substituted isocoumarins under mild conditions was reported. A variety of substrates were applied in this reaction in yields up to 89%.
