128812-16-8Relevant articles and documents
Propargylation of CoQ0 through the Redox Chain Reaction
Mlynarski, Jacek,Pawlowski, Robert,Stodulski, MacIej
, (2022/01/04)
An efficient catalytic propargylation of CoQ0 is described by employing the cooperative effect of Sc(OTf)3 and Hantzsch ester. It is suggested to work through the redox chain reaction, which involves hydroquinone and dimeric propargylic moiety intermediates. A broad range of propargylic alcohols can be converted into the appropriate derivatives of CoQ0 containing triple bonds in good to excellent yields. The mechanism of the given transformation is also discussed.
Redox-Neutral Arylations of Vinyl Cation Intermediates
Kaiser, Daniel,Veiros, Luis F.,Maulide, Nuno
supporting information, p. 64 - 77 (2017/01/14)
Herein we present a new unified concept for C?C bond formation under redox-neutral conditions. Our strategy hinges upon interception of a vinyl cation with a sulfoxide resulting in simultaneous C–C and C?O bond formation and arylation. A range of structurally diverse vinyl cations are generated in situ in the presence of a sulfoxide, resulting in hydrative arylation, direct arylation of enol triflates and interrupted Meyer–Schuster rearrangement. Mechanistic investigations showcase the crucial role played by the fleeting vinyl cation intermediate and structural features that lead to its stabilization. Applications of the reaction products to synthesis are also presented. (Figure presented.).
Palladium-Catalyzed Synthesis of Conjugated Allenynes via Decarboxylative Coupling
Smith, Mary K.,Tunge, Jon A.
supporting information, p. 5497 - 5500 (2017/10/25)
A new strategy to access conjugated allenynes via a decarboxylative coupling of propargyl esters of propiolates has been developed. In this process, allenyl-palladium intermediates are coupled with acetylides that are generated in situ to form the conjuga
Synthesis of enantiopure C3-symmetric bulky trialkanolamines and their enantioselective inductivity during the alkynylation of aldehydes
Zhang, An-Lin,Yang, Li-Wen,Yang, Nian-Fa,Zhang, Jing
, p. 88 - 93 (2014/12/11)
Several C3-symmetric trialkanolamines can be efficiently obtained via molecular sieve-assisted epoxide ring opening with ammonia in high yields (up to 90%) and regioselectivity up to 100%. These trialkanolamines were effective for the asymmetri
A concise access to (polyfluoroaryl)allenes by Cu-catalyzed direct coupling with propargyl phosphates
Nakatani, Akihiro,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
experimental part, p. 2586 - 2589 (2012/07/30)
A copper-based catalyst system for the direct coupling of polyfluoroarenes with propargyl phosphates has been developed. The catalysis can provide a rapid and concise access to (polyfluoroaryl)allenes, which can be important building blocks for the synthesis of fluorinated functional materials.
Asymmetric direct alkynylation catalyzed by chiral ru-bis(oxazolinyl)phenyl complexes
Ito, Jun-Ichi,Asai, Ryosuke,Nishiyama, Hisao
supporting information; experimental part, p. 3860 - 3862 (2010/11/17)
Propargylic alcohols were obtained with excellent enantioselectivities in the asymmetric direct alkynylation of aldehydes using 5 mol % of chiral ruthenium complexes containing the chiral bis(oxazolinyl)phenyl ligand.
Gold-catalyzed efficient preparation of linear α-haloenones from propargylic acetates
Yu, Meng,Zhang, Guozhu,Zhang, Liming
experimental part, p. 1846 - 1855 (2009/07/04)
Versatile linear α-iodo- and α-bromoenones are prepared efficiently from readily accessible propargylic acetates using 2 mol % of Au(PPh3)NTf2. This reaction is easy to execute and has broad substrate scope. Good to excellent Z-selectivities are observed in the cases of propargylic acetates derived from aliphatic aldehydes.
Gold-catalyzed efficient preparation of linear α-lodoenones from propargylic acetates
Yu, Meng,Zhang, Guozhu,Zhang, Liming
, p. 2147 - 2150 (2008/02/03)
Only 2 mol % of Au(PPh3)NTf2 is needed to convert readily accessible propargylic acetates into versatile linear α-iodoenones in good to excellent yields. This reaction is easy to execute and has broad substrate scope. Good to excellent Z-selectivities are observed in the cases of aliphatic propargylic acetates derived from aldehydes.
Bisoxazolidine-catalyzed enantioselective alkynylation of aldehydes
Wolf, Christian,Liu, Shuanglong
, p. 10996 - 10997 (2007/10/03)
A C2-symmetric bisoxazolidine derived from aminoindanol has been successfully applied in the asymmetric alkynylation of aldehydes. The ligand is readily available, has a wide substrate scope, and catalyzes the formation of chiral propargylic alcohols with excellent yields and enantioselectivties. Copyright
Tandem Au-catalyzed 3,3-rearrangement-[2 + 2] cycloadditions of propargylic esters: Expeditious access to highly functionalized 2,3-indoline-fused cyclobutanes
Zhang, Liming
, p. 16804 - 16805 (2007/10/03)
The treatment of readily available propargylic indole-3-acetates with a catalytic amount of AuCl(PPh3)/AgSbF6 leads to tandem activations of the propargylic esters and the in situ generated allenylic esters, resulting in expeditious access to highly functionalized cyclobutanes with fused 2,3-indoline and γ-lactone rings and an exocyclic E-double bond through sequential 3,3-rearrangement and [2 + 2] cyclization. Copyright
