92078-65-4

Upstream product

• 111-24-0 1,5-dibromo-pentane 
• 536-74-3 phenylacetylene 
• 4440-01-1 lithium phenylacetylide 
• 34626-51-2 5-bromopentan-1-ol 
• 103935-50-8 5-bromopentyl trifluoromethanesulfonate 

Downstream Products

• 1608-31-7 (cyclohexylidenemethyl)benzene 
• 19016-85-4 hept-6-en-1-ynylbenzene 
• 14374-45-9 1-heptynylbenzene 
• 154188-77-9 2-(7-Phenyl-hept-6-ynyl)-isoindole-1,3-dione 
• 1454697-98-3 9-phenylnon-8-ynenitrile 
• 1454697-37-0 5-fluoro-9-phenyl-1,2,3,4-tetrahydroacridine 
• 1454697-35-8 9-phenyl-7-(trifluoromethyl)-1,2,3,4-tetrahydroacridine 
• 1256344-76-9 2-bromo-9-phenyl-5,6,7,8-tetrahydroacridine 
• 116690-69-8 6-chloro-10-phenyl-1,2,3,4-tetrahydroacridine 
• 1454697-39-2 7-fluoro-9-phenyl-1,2,3,4-tetrahydroacridine 
• 585510-17-4 7-methyl-9-phenyl-1,2,3,4-tetrahydroacridine 
• 10265-83-5 9-phenyl-1,2,3,4-tetrahydroacridine 
• 1311380-61-6 C₂₂H₂₀ClNO 
• 1311380-62-7 C₂₂H₂₀BrNO 

Relevant academic research and scientific papers

N-Heterocyclic carbene copper-catalyzed direct alkylation of terminal alkynes with non-activated alkyl triflates

(NHC)-Cu-catalyzed C(sp)-C(sp3) bond formation has been successfully achieved under mild conditions. Nonactivated alkyl triflates, which could be easily derived from alcohols, were utilized as C-O electrophiles. Mechanistic studies suggested th

Enabling the Use of Alkyl Thianthrenium Salts in Cross-Coupling Reactions by Copper Catalysis

Alkyl groups are one of the most widely used groups in organic synthesis. Here, a a series of thianthrenium salts have been synthesized that act as reliable alkylation reagents and readily engage in copper-catalyzed Sonogashira reactions to build C(sp3)?C(sp) bonds under mild photochemical conditions. Diverse alkyl thianthrenium salts, including methyl and disubstituted thianthrenium salts, are employed with great functional breadth, since sensitive Cl, Br, and I atoms, which are poorly tolerated in conventional approaches, are compatible. The generality of the developed alkyl reagents has also been demonstrated in copper-catalyzed Kumada reactions.

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

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

An unprecedented tandem annulation of ω-azido-1-alkynes with diaryl-iodonium salts: A facile synthesis of polycyclic quinolines

Polysubstituted quinolines are synthesized through an unprecedented cascade annulation of ω-azido-1-alkynes with diaryliodonium salts, which serve as C2-building blocks. The reaction proceeds smoothly and is catalyzed by Cu(I) catalysts to give various qu

A concise construction of polycyclic quinolines via annulation of ω-cyano-1-alkynes with diaryliodonium salts

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.

Catalytic reduction of phenyl-conjugated acetylenic halides by nickel(I) salen: Cyclization versus coupling

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.

Organolanthanide-catalyzed intramolecular hydroamination/cyclization of aminoalkynes

This contribution reports the efficient and regiospecific Cp'2LnCH(SiMe3)2 (Ln = La, Nd, Sm, Lu; Cp' = η5-Me5C5)- and Me2SiCp''2LnCH(SiMe3)2 (Ln = Nd, Sm; Cp'' = η5-Me4C5)-catalyzed hydroamination/cyclization of aliphatic and aromatic aminoalkynes of the formula RC≡C(CH2)(n)NH2 to yield the corresponding cyclic imines RCH2C=N(CH2)(n-1)CH2, where R, n, N(t) h-1 (°C) = Ph, 3, 77 (21°C); Ph, 3, 2830 (60°C); Me, 3, 96 (21°C); CH2=CMeCH2, 3, 20 (21°C); H, 3, 580 (21°C); Ph, 4, 4 (21°C); Ph, 4, 328 (60°C); Ph, 5, 0.11 (60°C); and SiMe3, 3, >7600 (21°C), and of aliphatic secondary amino-alkynes of the formula RC≡C(CH2)3NHR1 to generate the corresponding cyclic enamines RCH=CNR1(CH2)2CH2 where R, R1, N(t) h-1 (°C) = SiMe3, CH2=CHCH2, 56 (21°C); H, CH2=CHCH2, 27 (21°C); SiMe3, CH2=CH(CH2)3, 129 (21°C); and H, CH2=CH(CH2)3, 47 (21°C). Kinetic and mechanistic evidence is presented arguing that the turnover-limiting step is an intramolecular alkyne insertion into the Ln-N bond followed by rapid protonolysis of the resulting Ln-C bond. The use of larger metal ionic radius Cp'2LnCH(SiMe3)2 and more open Me2SiCp''2LnCH(SiMe3)2 complexes as the precatalysts results in a decrease in the rate of hydroamination/cyclization, arguing that the steric demands in the -C≡C- insertive transition state are relaxed compared to those of the analogous aminoolefin hydroamination/cyclization.

Cyclizations of ω-Alkynyl Halides by Cr(II) Reduction

Reduction of halides of the types RCC(CH2)nX with Cr(II) in aqueous DMF containing ethylenediamine proceeds by way of the intermediate radicals which cyclize regioselectively in the n=4 and n=5 cases to give substituted methylenecycloalkanes.Experimental conditions which favor longer lifetimes for the intermediate radicals (low concentrations, slow addition times, and an inverse-addition mode) result in increased cyclization.The iodides curiously give more cyclic product than the corresponding bromides.These results are discussed.