886-66-8Relevant articles and documents
A base-promoted tandem approach to bicyclic 8-membered ring ketones
dos Santos, Emerson E. F.,de Souza, Gabriela F. P.,Simoni, Deborah A.,Salles, Airton G.
, p. 3249 - 3253 (2020)
A base-promoted tandem route toward unprecedented bicyclic 8-membered ring ketones is reported. Under our approach, the targeted products are delivered in high yields from phenylacetylenes and 1,3-diketones. The method has a good scope and gives access to a complex structure that offers a wealth of opportunities for further functionalization.
Enantioselective Decarboxylative α-Alkynylation of β-Ketocarbonyls via a Catalytic α-Imino Radical Intermediate
Wang, Dehong,Zhang, Long,Luo, Sanzhong
, p. 4924 - 4927 (2017)
A distinctive aminocatalysis via α-imino radical is reported on the basis of SET oxidation of a secondary enamine. The combination of chiral primary amine catalysis and visible-light photoredox catalysis enables the enantioselective decarboxylative coupling of propiolic acid and β-ketocarbonyls to afford alkynylation adducts with high enantioselectivity. Mechanism studies indicate the reaction proceeds via an α-imino radical addition.
Selective Carboxylate Directed ortho Functionalization in Copper Catalyzed Reactions of Polyiodo Aromatics: A Straightforward Preparation of 5,7-Diiodo-1H-isochromen-1-ones
Anselmi, Elsa,Bahlaouan, Zineb,Inack Ngi, Samuel,Parrain, Jean Luc,Magnier, Emmanuel,Abarbri, Mohamed
, p. 6131 - 6136 (2017)
A facile, and totally regioselective one-pot approach to synthesize 5,7-diiodo-3-substituted-isocoumarins is described. This reaction was realized by using copper iodide as the catalyst under mild reaction conditions. The methodology was used to design a wide variety of compounds and was tolerant to a large number of functional groups. Interestingly, among the three possible carbon–iodine bonds, only one was reactive, which left the two others intact for further functionalization.
Selective synthesis of 2-aryl-3-alkenylindoles and 2-aryl-3-alkynylindoles by palladium-catalyzed ligand-promoted annulative coupling of anilines and propargyl alcohols
Li, Qiang,Xia, Ying,Yan, Xufei,Zhou, Xiangge,Zhu, Maoshuai
, (2021)
A palladium-catalyzed annulative reaction between aniline and propargyl alcohol has been developed. Propargyl alcohols act as internal or terminal alkynes in the reactions through C?H/C?C activation in the presence of Ac-Gly-OH or Xantphos as ligand, resulting in the formation of 3-alkenylindoles or 3-alkynylindoles respectively. The incorporated alkenyl and alkynyl groups could be engaged for further derivations to form versatile indole skeletons with potential applications.
Unusual Transformations of Highly Unsaturated Trifluoromethanesulfonamide Derivatives
Ushakova,Shainyan
, p. 351 - 353 (2019)
Oxidative condensation of N,N-bis(prop-2-yn-1-yl)trifluoromethanesulfonamide in DMSO involved only one ethynyl group, whereas in aqueous methanol 1,8-bis(trifluoromethanesulfonyl)-1,8-diazacyclotetradeca-3,5,10,12-tetrayne was obtained. N,N′-(Hexa-2,4-diyn-1,6-diyl)bis(trifluoromethanesulfonamide) in hexane solution was unexpectedly converted to diphenyldiacetylene, presumably, as a result of annulation of highly unsaturated carbon chains in the initial polyacetylene molecule and elimination of trifluoromethanesulfonamide and trifluoromethanesulfonamidomethyl residues.
Synthesis and spectroscopic characterization of ?-bonded phenothiazinonepalladium complexes
Konishi, Hisatoshi,Matsumura, Chisato,Okano, Tamon,Kiji, Jitsuo
, p. 245 - 248 (1989)
Treatment of 4-iodo-3H-phenothiazin-3-one with tetrakis(triphenylphosphine)palladium(0) in boiling benzene yields trans-iodo(3H-phenothiazin-3-one-4-yl)bis(triphenylphosphine)palladium(II) by oxidative addition. 5H-Benzo>phenothiazin-5-one-6-yl complex is prepared in a similar manner.The ?-bonded iminoquinone structure of the complexes has been elucidated by 1H, 13C, and 31P NMR spectroscopy.
Cu(OAc)2-catalysed oxidative dual C-H/N-H activation of terminal alkynes and N-deprotected sulfonimidamides: An easy access to N-alkynylated sulfonimidamides
Nandi, Ganesh Chandra,Kota, Sudhakar Rao,Naicker, Tricia,Govender, Thavendran,Kruger, Hendrick G.,Arvidsson, Per I.
, p. 2861 - 2867 (2015)
We report a mild and efficient Cu(OAc)2-catalysed protocol for the oxidative C-N cross-coupling of terminal alkynes and N-deprotected sulfonimidamides. The reaction leads to hitherto unknown N-alkynylated sulfonimidamides. Furthermore, we found that the synthesised N-alkynylated sulfonimidamides could undergo silica-gel-mediated hydrolysis to give the corresponding N-acyl-sulfonimidamides, as well as borane-dimethyl sulfide-mediated reduction to give the corresponding N-alkylated sulfonimidamides.
Aerobic Copper Catalysis for Tandem Oxy-N-alkenylation of [1,2,3]Triazolo[1,5-a]pyridines
Pankajakshan, Sreekumar,Ang, Wei Li,Sreejith, Sivarampanicker,Stuparu, Mihaiela Corina,Loh, Teck-Peng
, p. 3034 - 3038 (2016)
N-Alkenylated triazolinone ylides were generated through copper-catalyzed oxy-N-alkenylation of triazolopyridines. The mechanistic course of this aerobic tandem reaction has been experimentally elucidated and primary photophysical data of the ylide products are also given. (Figure presented.).
Rhodium-catalyzed annulative coupling of: N-aryl-2-aminopyridine and propargylic amine via selective C-C and C-H bond activation
He, Shiyu,Yan, Xufei,Lei, Yanxi,Xiang, Haifeng,Zhou, Xiangge
, p. 2284 - 2287 (2020)
A Rh(iii)-catalyzed/Cu(ii)-mediated cascade reaction between N-aryl-2-aminopyridine and propargylic amine has been developed. Selective C(sp2)-H bond activation and C(sp)-C(sp3) cleavage occurred during the reaction, which was followed by a cyclization reaction to provide an unprecedented synthetic route to form 1,2-disubstituted indoles in yields up to 85%.
CuI-Mediated Bromoalkynylation and Hydroalkynylation Reactions of Unsymmetrical Benzynes: Complementary Modes of Addition
Xiao, Xiao,Wang, Tao,Xu, Feng,Hoye, Thomas R.
, p. 16564 - 16568 (2018)
Benzynes formed by heating a suitable triyne (or tetrayne) substrate are shown to react with in situ generated alkynyl copper species. The latter are compatible with the polyyne substrates and two types of chemistries have been achieved: (i) 1-bromo-1-alkynes efficiently undergo net bromoalkynylation of the (unsymmetrical) benzynes and (ii) in situ generated alkynylcopper species give rise to hydroalkynylation products. The regiochemical preferences of these two modes of reaction are complementary to one another with respect to the position of alkynyl substituent in the final products.
Copper-catalyzed decarboxylative Se insertion coupling of indoles and propiolic acids
Wang, Caihong,Wu, Ge,Zhou, Xueying
, (2022/02/02)
A novel and efficient copper-catalyzed decarboxylative alkynylselenation of indoles with Se powder and propiolic acids has been developed. The outstanding advantages of this protocol not only nicely avoid the use of prefabricated arylselenation reagent and address the facile over-selention issues, but also enrich the chemistry of selenium powder. Importantly, this reaction could be extended to pyrrole, and the practical utility of this transformation has been demonstrated in gram-scale synthesis and late-stage indolylselenation of Clofibrate-derived propiolic acid.
One-Pot Dual C?C Coupling Reaction via Site Selective Cascade Formation by PdII-Cryptate of an Amino-Ether Heteroditopic Macrobicycle
Sarkar, Sayan,Sarkar, Piyali,Munshi, Sandip,Ghosh, Pradyut
, p. 7307 - 7314 (2021/03/22)
Selectivity of aryl iodo over ethynyl iodo toward the Suzuki cross coupling reaction is explored by utilizing a palladium complex of amino-ether heteroditopic macrobicycle. Subsequently, unreacted ethynyl iodide undergoes homocoupling reaction in the same catalytic atmosphere, thereby representing a cascade dual C?C coupling reaction. Furthermore, this approach is extended for novel one-pot synthesis of unsymmetrical 1,3-diynes.
Glycosyl Triazole Ligand for Temperature-Dependent Competitive Reactions of Cu-Catalyzed Sonogashira Coupling and Glaser Coupling
Mishra, Nidhi,Singh, Sumit K.,Singh, Anoop S.,Agrahari, Anand K.,Tiwari, Vinod K.
, p. 17884 - 17895 (2021/12/17)
Glycosyl triazoles have been introduced as efficient ligands for the Cu-catalyzed Sonogashira reaction to overcome the challenges of sideways homocoupling reactions in Cu catalysis in this reaction. The atmospheric oxygen in a sealed tube did not affect t
