609769-61-1Relevant articles and documents
Zn(II)-Catalyzed One-Pot Synthesis of Coumarins from Ynamides and Salicylaldehydes
Yoo, Huen Ji,Youn, So Won
supporting information, p. 3422 - 3426 (2019/05/10)
A highly efficient and straightforward synthesis of diversely substituted coumarins from ynamides and salicylaldehydes in the presence of Zn(II) catalyst has been developed. The sulfonamide moiety of ynamides was successfully recycled in this process, serving as an effective traceless directing group for high regioselectivity in the bond-forming event. The advantages of this protocol are good functional group tolerance, broad substrate scope, simple and high-yielding reaction, recovery/reuse of the sulfonamides, low catalyst loading of inexpensive catalyst, and, by these merits, a more cost-effective and greener process.
Highly Selective Syn Addition of 1,3-Diones to Internal Ynamides Catalyzed by Zinc Iodide
Plamont, Rémi,Graux, Lionel V.,Clavier, Hervé
, p. 1372 - 1376 (2018/04/02)
1,3-Diones are already established as nucleophiles to perform additions to ynamides; the highly selective hydroalkoxylation of internal ynamides is now described. Several catalytic systems have been compared to perform this transformation, including transition-metal-based catalysts and Lewis acids. ZnI2 was found to be both very active and highly selective providing only E adducts through a syn addition. Investigation of the scope and limitations showed that this catalyst was compatible with various functional groups. In addition to seventeen examples of ynamide hydroalkoxylation, one example of ynamide hydroarylation is reported.
A Highly Regio- and Stereoselective Syntheses of α-Halo Enamides, Vinyl Thioethers, and Vinyl Ethers with Aqueous Hydrogen Halide in Two-Phase Systems
Cao, Wei,Chen, Ping,Wang, Liang,Wen, Hao,Liu, Yu,Wang, Wanshu,Tang, Yu
supporting information, p. 4507 - 4511 (2018/08/09)
A metal-free regio- and stereoselective method is achieved for the preparation of (E)-configured α-halo enamides, vinyl thioethers, and vinyl ethers using aqueous HX (X = F, Cl, Br, I), which features high functional group compatibility and regio- and stereoselectivity, mild conditions, high efficiency, and rapid transformation. Additionally, the isomers could be yielded readily from the (E)-configured α-halo enamides via photocatalysis or under Sonogashira coupling conditions.
N-Substitution dependent stereoselectivity switch in palladium catalyzed hydroalkynylation of ynamides: A regio and stereoselective synthesis of ynenamides
Dwivedi, Vikas,Hari Babu, Madala,Kant, Ruchir,Sridhar Reddy, Maddi
, p. 14996 - 14999 (2015/10/12)
A highly general palladium catalysed regioselective hydroalkynylation of ynamides for versatile enamide building blocks with an alkyne tether is achieved with an N-substitution dependent stereoselectivity switch under very mild reaction conditions.
Syntheses of α-stannylated and α-iodinated enamides via molybdenum-catalyzed hydrostannation
Maity, Pulakesh,Klos, Manuel R.,Kazmaier, Uli
supporting information, p. 6246 - 6249 (2014/01/17)
α-Stannylated and α-iodinated enamides can easily be obtained by molybdenum-catalyzed regio- and stereoselective hydrostannation and subsequent tin-iodine exchange. These functionalized enamides are interesting building blocks for a wide range of cross-coupling reactions giving access to various types of α-substituted enamides.
Preparation of 3,4,5-trisubstituted oxazolones by pd-catalyzed coupling of n -alkynyl tert -butyloxycarbamates with aryl halides and related electrophiles
Lu, Zenghui,Cui, Weijian,Xia, Siyuan,Bai, Yihui,Luo, Fang,Zhu, Gangguo
, p. 9871 - 9877,7 (2012/12/12)
A novel palladium-catalyzed approach for the assembly of 3,4,5-trisubstituted oxazolones has been achieved by the coupling of N-alkynyl tert-butyloxycarbamates with aryl halides and related electrophiles, which involves an oxidative addition followed by oxypalladation/reductive elimination. The reaction provides a convenient access to diversely substituted oxazolones in satisfactory yields and shows good functional group compatibility.
Copper-catalyzed coupling of 1,2-dibromo-1-styrenes with sulfonamides for the preparation of ynamides
Yang, Yuan,Zhang, Xiaoyun,Liang, Yun
supporting information, p. 6557 - 6560,4 (2012/12/11)
Ynamides were prepared through an efficient copper-catalyzed coupling reaction. In the presence of copper iodide, 1,10-phenanthroline, and Cs 2CO3, the coupling reaction of 1,2-dibromo-1-styrenes with sulfonamides proceeded smoothly
Synthesis of functionalized oxazolones by a sequence of Cu(ll)- And Au(l)-catalyzed transformations
Istrate, Florin M.,Buzas, Andrea K.,Jurberg, Igor Dias,Odabachian, Yann,Gagosz, Fabien
supporting information; experimental part, p. 925 - 928 (2009/04/07)
A study concerning a two-step sequence leading to the formation of diversely 1,5-disubstituted oxazolones is described. The mild conditions employed allow the efficient and rapid synthesis of a variety of such compounds via an initial Cu(II)-catalyzed coupling of a bromoalkyne with a secondary tert-butyloxycarbamate followed by a Au(l)-catalyzed cycloisomerization of the N-alkynyl tert-butyloxycarbamates thus obtained.
Ruthenium-catalyzed [2 + 2] cycloadditions of bicyclic alkenes and ynamides
Villeneuve, Karine,Riddell, Nicole,Tam, William
, p. 3823 - 3836 (2007/10/03)
Ruthenium-catalyzed [2 + 2] cycloadditions between bicyclic alkenes and ynamides were investigated. The ynamide moiety was found to be compatible with the ruthenium-catalyzed cycloaddition conditions giving the corresponding cyclobutene cycloadducts in moderate to good yields (up to 97%). Diastereoselective cycloaddition utilizing chiral cyclic ynamides were also examined and a low to moderate level of asymmetric induction was observed.
Ruthenium-catalyzed [2 + 2] cycloadditions of ynamides
Riddell, Nicole,Villeneuve, Karine,Tam, William
, p. 3681 - 3684 (2007/10/03)
(Chemical Equation Presented) Ruthenium-catalyzed [2 + 2] cycloadditions between norbornene and ynamides were investigated. The ynamide moiety was found to be compatible with the ruthenium-catalyzed cycloaddition conditions, giving the corresponding cyclobutene cycloadducts in moderate to good yields (up to 97%).
