57718-13-5Relevant academic research and scientific papers
Accessing Polycyclic Heteroarenes Enabled by Copper-Catalyzed Aerobic Oxidative C–H/C–H [4 + 2] Annulation of 3-Arylindole Derivatives
Yue, Yuanyuan,Yang, Yan,Sun, Chunying,Chao, Junli,Ye, Yaqing,Guo, Xiaohui,Liu, Jianming
supporting information, p. 478 - 483 (2022/01/20)
Several polycyclic aromatic hydrocarbons are delivered at room temperature by copper-catalyzed aerobic oxidative C–H/C–H [4 + 2] annulation of alkyl-substituted 3-arylindole derivatives. Specifically, dual aryl C–H functionalization is furnished under mil
Rhodium-catalyzed intramolecular cascade sequence for the formation of fused carbazole-annulated medium-sized rings by cleavage of C(sp2)-H/C(sp3)-H bonds
Li, Qiuyun,Li, Bin,Wang, Baiquan
supporting information, p. 9147 - 9150 (2018/08/23)
The rhodium(iii)-catalyzed intramolecular annulation of alkyne-tethered 3-(indol-3-yl)-3-oxopropanenitriles for the synthesis of fused carbazole scaffolds via C-H activation has been developed. A series of six-, seven-, and eight-membered hydroazepino[3,2
A concise construction of polycyclic quinolines via annulation of ω-cyano-1-alkynes with diaryliodonium salts
Wang, Yong,Chen, Chao,Zhang, Shu,Lou, Zhenbang,Su, Xiang,Wen, Lirong,Li, Ming
supporting information, p. 4794 - 4797 (2013/10/08)
A concise construction of polycyclic quinolines via intramolecular [2 + 2 + 2] annulation of ω-cyano-1-alkynes with diaryliodonium salts was realized. The process produced polycyclic quinolines in high yields with readily available staring materials and was tolerated with halogen substituents.
One-pot synthesis of benzo[f]quinolin-3-ones and benzo[a]phenanthridein-5- ones by the photoanuulation of 6-chloropyridin-2-ones and 3-chloroisoquinolin-1- ones to phenylacetylene
Wang, Ren,Lu, Shen-Ci,Zhang, Yi-Ming,Shi, Zong-Jun,Zhang, Wei
supporting information; experimental part, p. 5802 - 5808 (2011/10/02)
The one-pot synthesis of benzo[f]quinolin-3-ones and benzo[a] phenanthridein-5-ones was achieved by the inter- and intramolecular photoannulation of 6-chloropyridin-2-ones and 3-chloroisoquinolin-1-ones with phenylacetylene or tethered phenylacetylene. The reactions were proceeded by photoaddition of 6-chloropyridin-2-ones and 3-chloroisoquinolin-1-ones to phenylacetylene to give the chlorine-substituted stilbenoids, and then 6π electrocyclization of the stilbenoids and oxidation aromatization to afford the polycyclic products.
The versatile role of norbornene in C-H functionalization processes: concise synthesis of tetracyclic fused pyrroles via a threefold domino reaction
Gericke, Kersten M.,Chai, David I.,Lautens, Mark
, p. 6002 - 6014 (2008/12/20)
The synthesis of novel tetracyclic fused pyrroles from 1-(2-iodophenyl)-1H-pyrrole and various bromoalkyl-aryl alkynes via a palladium(0)-catalyzed and norbornene-mediated threefold domino reaction is reported. PdCl2 and tri-2-furylphosphine (TFP) in the presence of norbornene and Cs2CO3 in CH3CN at 90 °C gave a variety of tetracyclic fused pyrroles in usually high yields. In the described reaction sequence two of the three carbon-carbon bonds are formed by functionalization of an unactivated aryl C-H bond.
Catalytic reduction of phenyl-conjugated acetylenic halides by nickel(I) salen: Cyclization versus coupling
Mubarak, Mohammad S.,Jennermann, Theodore B.,Ischay, Michael A.,Peters, Dennis G.
, p. 5346 - 5352 (2008/03/14)
Cyclic voltammetry and controlled-potential electrolysis were employed to study the catalytic reduction of five phenyl-conjugated haloalkynes by nickel(I) salen electro-generated at carbon cathodes in dimethylformamide containing tetramethylammonium tetrafluoroborate. Electrocatalytic reduction of 7-bromo- and 7-iodo-1-phenyl-1-heptyne affords the carbocyclic product, benzylidenecyclohexane, in up to 41 % yield, whereas under similar conditions reduction of 5-halo-1-phenyl-1-pentyne and 8-bromo-1-phenyl-1-octyne gives benzylidenecyclobutane and benzylidenecycloheptane, respectively, in very low yield (≤1 %). Dimers, alkynes, and alkenynes are other products formed from the phenyl-conjugated haloalkynes. Dimers (diphenylalkadiynes) derived from 5-halo-1-phenyl-1-pentyne and 8-bromo-1-phenyl-1-octyne are obtained in yields ranging from 85 to 93 %, whereas 1,14-diphenyltetradeca-1,13-diyne (the dimer produced from 7-halo-1-phenyl-1-heptyne) is found in yields of 45-51 %. To account for the formation of the various products, a mechanistic scheme that involves phenyl-conjugated alkynyl radicals arising from nickel(I) salen catalyzed cleavage of the carbon-halogen bond of each substrate was formulated. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Rh(I)-catalyzed CO gas-free cyclohydrocarbonylation of alkynes with formaldehyde to α,β-butenolides
Fuji, Koji,Morimoto, Tsumoru,Tsutsumi, Ken,Kakiuchi, Kiyomi
, p. 3295 - 3297 (2007/10/03)
The rhodium(I)-catalyzed reaction of alkynes with formaldehyde proceeds via the double incorporation of a carbonyl moiety from formaldehyde, resulting in a CO gas-free cyclohydrocarbonylation leading to α,β-butenolides. The Royal Society of Chemistry 2005.
AuBr3- and Cu(OTf)2-catalyzed intramolecular [4 + 2] cycloaddition of tethered alkynyl and alkenyl enynones and enynals: A new synthetic method for functionalized polycyclic hydrocarbons
Asao, Naoki,Sato, Kenichiro,Menggenbateer,Yamamoto, Yoshinori
, p. 3682 - 3685 (2007/10/03)
(Chemical Equation Presented) Treatment of tethered alkynyl enynones 8, in which a carbon chain is attached to the carbonyl group, with a catalytic amount of AuBr3in (ClCH2)2 gave the naphthyl ketones 9 in good to high yields (top-down approach). Analogously, the AuBr 3-catalyzed benzannulations of 10, in which a carbon tether is extended from the alkynyl terminus, also proceeded smoothly, and the cyclized naphthyl ketones 11 were obtained in high yields (bottom-up approach). Similarly, when two kinds of tethered alkenyl enynones 12 and 14 were treated with Cu(OTf)2 catalyst, the corresponding dihydronaphthyl ketone products 13 and 15 were obtained in high yields, respectively. The present formal [4 + 2] intramolecular cycloaddition proceeds most probably through the coordination of the triple bond at the ortho position of substrates to Lewis acids, the formation of benzopyrylium ate complex 16 via the nucleophilic addition of the carbonyl oxygen atom, the reverse electron demand type Diels-Alder addition of the tethered alkynes or alkenes to the ate complex, and subsequent bond rearrangement.
Organolanthanide-catalyzed intra- and intermolecular tandem C-N and C-C bond-forming processes of aminodialkenes, aminodialkynes, aminoalkeneynes, and aminoalkynes. New regiospecific approaches to pyrrolizidine, indolizidine, pyrrole, and pyrazine skeleto
Li, Yanwu,Marks, Tobin J.
, p. 1757 - 1771 (2007/10/03)
This contribution describes catalytic tandem C-N and C-C bond-forming reactions involving the intramolecular hydroamination/bicyclization and intermolecular hydroamination/cyclization of olefins and alkynes using the organolanthanide complexes Cp'2/
Organocobaloxime in organic synthesis: efficient trapping of 5-phenylpent-4-ynyl radical by useful functional groups
Das, Indira,Roy, Sujit
, p. 233 - 238 (2007/10/02)
5-Phenylpent-4-ynyl cobaloxime, R(CoIII) reacts with the free radical precursors XY under thermal or photochemical conditions to give the corresponding organic product RX or RY, depending on the precursor.A non-chain radical mechanism is invoked to account for the product distribution. Key words: Cobaloxime; Radical
