913192-84-4Relevant academic research and scientific papers
Gold-catalyzed Intermolecular Oxidations of 2-Ketonyl-1-ethynyl Benzenes with N-Hydoxyanilines to Yield 2-Aminoindenones via Gold Carbene Intermediates
Mokar, Bhanudas Dattatray,Huple, Deepak B.,Liu, Rai-Shung
supporting information, p. 11892 - 11896 (2016/11/16)
Gold-catalyzed oxidations of 2-ketonyl-1-ethynyl benzenes with N-hydroxyanilines yield 2-aminoindenone derivatives efficiently. Experimental data suggests that this process involves an α-oxo gold carbene intermediate, generated from the attack of N-hydroxyaniline on furylgold carbene intermediate, rather than the typical attack of oxidants on π-alkynes.
Divergent C-H Insertion-Cyclization Cascades of N-Allyl Ynamides
Adcock, Holly V.,Chatzopoulou, Elli,Davies, Paul W.
, p. 15525 - 15529 (2016/01/26)
Gold carbene reactivity patterns were accessed by ynamide insertion into a C(sp3)-H bond. A substantial increase in molecular complexity occurred through the cascade polycyclization of N-allyl ynamides to form fused nitrogen-heterocycle scaffol
Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides: Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines
Yeh, Ming-Chang P.,Liang, Chia-Jung,Chen, Hsiao-Feng,Weng, Yu-Ting
supporting information, p. 3242 - 3254 (2015/11/03)
Indium(III)-catalyzed cyclization reactions of aromatic 5-enynamides were studied. Indium triflate enabled the efficient synthesis of 2-aminonaphthalenes and 2-amino-1H-indenes from aromatic N-methyl-N-tosyl-ynamides bearing an ortho-vinyl and -isobutenyl group, respectively. The aromatic N-3-arylpropargylynamides bearing an ortho-gem-dihalovinyl subunit underwent a tandem cyclization/carbobromination reaction in the presence of indium tribromide to provide the dibrominated 2,3-dihydro-1H-indeno[2,1-b]pyridine derivatives in good yields.
Gold-catalyzed carboalkoxylations of 2-ethynylbenzyl ethers to form 1- and 2-indanones chemoselectively: Effects of ligands and solvents
Wang, Chiou-Dong,Hsieh, Yi-Feng,Liu, Rai-Shung
supporting information, p. 144 - 152 (2014/03/21)
The selective syntheses of 1- and 2-indan-one compounds from 2-ethynylbenzyl ethers have been achieved with suitable catalysts and solvents. The highly acidic [tris(pentafluorophenyl)phos-phine]gold hexafluoroantimonate [(C6F5)3AuSbF6] in nitromethane (MeNO2) preferably gives 1-indan-ones whereas [(ortho-biphenyl) di(tert-butyl)phosphine] gold triflimide [(tBu)2(o-biphenyl) AuNTf2] in dichloroethane tends to form 2-indanone derivatives. For 2-indanone products, we isolated two indenyl methyl ethers for deuterium labeling analyses, providing evidence for p-alkyne activation.
1,2-N-migration in a gold-catalysed synthesis of functionalised indenes by the 1,1-carboalkoxylation of ynamides
Adcock, Holly V.,Langer, Thomas,Davies, Paul W.
supporting information, p. 7262 - 7266 (2014/06/23)
Unique α-hemiaminal ether gold carbene intermediates were accessed by a gold-catalysed 1,1-carboalkoxylation strategy and evolved through a highly selective 1,2-N-migration. This skeletal rearrangement gave functionalised indenes, and isotopic labelling c
Gold catalysis: Catalyst oxidation state dependent dichotomy in the cyclization of furan-yne systems with aromatic tethers
Hashmi, A. Stephen K.,Hofmann, Julia,Shi, Shuai,Schuetz, Alexander,Rudolph, Matthias,Lothschuetz, Christian,Wieteck, Marcel,Buehrle, Miriam,Woelfle, Michael,Rominger, Frank
, p. 382 - 389 (2013/02/25)
Four different synthetic strategies led to a variety of furan-yne systems that contained an aryl system in the tether. Due to the short routes to these systems (four steps or less), a small library of substrates could easily be prepared. These were treate
Gold-catalyzed formal cycloaddition of 2-ethynylbenzyl ethers with organic oxides and α-diazoesters
Pawar, Samir Kundlik,Wang, Chiou-Dong,Bhunia, Sabyasachi,Jadhav, Appaso Mahadev,Liu, Rai-Shung
, p. 7559 - 7563 (2013/07/26)
A world of possibilities: Gold-catalyzed reactions of 2-ethynylbenzyl ethers with organic oxides and α-diazoesters gave 1,3-dihydroisobenzofuran and naphthalene derivatives, respectively (see scheme; EWG=electron-withdrawing group). Mechanisms for the formation of the formal cycloadducts were elucidated by isotope labeling. Copyright
Synthesis of indenyl ethers by gold(I)-catalyzed intramolecular carboalkoxylation of alkynes
Dube, Pascal,Toste, F. Dean
, p. 12062 - 12063 (2007/10/03)
The gold(I)-catalyzed carboalkoxylation of alkynes to form indanone derivatives from readily available ortho-acetylenic benzylic ethers is described. Importantly, the gold(I)-catalyzed rearrangement of enantioenriched benzylic ethers proceeds with chirali
PtBr2-catalyzed transformation of allyl(o-ethynylaryl)carbinol derivatives into functionalized indenes. Formal sp3 C-H bond activation
Bajracharya, Gan B.,Pahadi, Nirmal K.,Gridnev, Ilya D.,Yamamoto, Yoshinori
, p. 6204 - 6210 (2007/10/03)
The PtBr2-catalyzed reaction of 1-ethynyl-2-(1-alkoxybut-3-enyl) benzenes at 120 °C in CH3CN gave functionalized indenes in good to allowable yields. Most probably, the hydrogen at the terminal alkyne is transferred to the adjacent internal β-carbon to form an (η2-vinylidene)platinum carbene intermediate, which activates the sp3 C-H bond at the benzylic carbon. This reaction pathway is supported by DFT calculations which suggest that the formation of the Pt-vinylidene complex is the rate-limiting stage for the whole transformation.
A novel tandem [2 + 2] cycloaddition-Dieckmann condensation with ynolate anions. Efficient synthesis of substituted cycloalkenones and naphthalenes via formal [n + 1] cycloaddition
Shindo,Sato,Shishido
, p. 7818 - 7824 (2007/10/03)
A novel tandem [2 + 2] cycloaddition-Dieckmann condensation via ynolate anions is described. Ynolate anions are useful for the formation of reactive β-lactone enolates via a pathway not involving the enolization of the corresponding β-lactones. The [2 + 2] cycloaddition of ynolate anions with δ- or σ-keto esters, followed by Dieckmann condensation, gives bicyclic β-lactones, which are easily decarboxylated to produce synthetically useful 2,3-disubstituted cyclopentenones and cyclohexenones in one pot. This tandem reaction was applied to a novel, one-pot synthesis of highly substituted naphthalenes.
