66898-41-7

Upstream product

• 2051-49-2 n-hexanoic anhydride 
• 90-02-8 salicylaldehyde 
• 271-89-6 1-benzofurane 
• 109-72-8 n-butyllithium 
• 124-38-9 carbon dioxide 
• 201230-82-2 carbon monoxide 
• 125345-27-9 2-(hex-1-yn-1-yl)phenol 
• 69626-75-1 2-iodobenzofuran 
• 533-58-4 2-Iodophenol 
• 693-02-7 hex-1-yne 
• 80778-47-8 1-iodo-2-methoxymethoxybenzene 
• 125345-26-8 1-hexynyl-2-(methoxymethoxy)benzene 
• 143-16-8 dihexylamine 
• 91-64-5 coumarin 

Relevant academic research and scientific papers

Visible Light-Induced Regioselective Decarboxylative Alkylation of the C(sp2)?H Bonds of Non-Aromatic Heterocycles

With sunlight or blue LEDs irradiation, regioselective decarboxylative alkylation of various non-aromatic heterocycles has been realized via C(sp3)-centered radical C(sp2)?C(sp3) bond formation under oxidant-free condition

Visible-light-driven copper-catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones and terminal alkynes: Regioselective synthesis of 3-arylcoumarins

We present the first example of sustainable, intuitive, highly regioselective, visible-light-driven copper catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones with terminal alkynes for the preparation of 3-arylcoumarins at room temperature. This operationally simple methodology has been successfully applied to a wide range of N-tosylhydrazones and alkynes (49 examples), and proceeds well to afford biologically active compounds, such as monoamine oxidase B (MAO-B) inhibitor and horseradish peroxidase (HRP) inhibitor, in satisfactory yields under mild conditions. Furthermore, mechanistic studies suggest that the reaction proceeds via a copper(ii)-superoxo or -peroxo complex mediated oxidative annulation of terminal alkynes, as evidenced by 18O2 isotopic-labelling experiments.

Visible-Light-Driven alkyne hydro-/carbocarboxylation using CO2 via iridium/cobalt dual catalysis for divergent heterocycle synthesis

We present herein the first visible-light-driven hydrocarboxylation as well as carbocarboxylation of alkynes using CO2 via an iridium/cobalt dual catalysis. Such transformations provide access to various pharmaceutically important heterocycles in a one-pot procedure from readily available alkynes. Coumarins, 2-quinolones, and 2-benzoxepinones were directly accessed through a one-pot alkyne hydrocarboxylation/alkene isomerization/cyclization sequence in which the Ir photocatalyst serves a dual role to promote single-electron transfer in alkyne hydrocarboxylation and energy transfer in the subsequent alkene isomerization. Moreover, an unprecedented cobalt carboxylation/acyl migration cascade enables alkyne difunctionalization to introduce γ-hydroxybutenolides with high efficiency. We expect that this cascade strategy will inspire new perspectives for alkyne and alkene difunctionalization.

Direct β-C(sp3)-H Functionalization of Aliphatic Amines to α,β-Unsaturated Imines, Aldehydes, and Chromenes

A metal-free method for direct β-C(sp3)-H functionalization of aliphatic amine was developed. The method is based on a reaction that yields enamine directly from the corresponding aliphatic amine, which otherwise requires the aid of metallic reagent and/or external oxidant. The reaction is operationally simple, general, and highly efficient in functionalizing both cyclic and acyclic amines. Structurally diverse unsaturated imines were obtained from N-heterocycles, while acyclic amines provided 2-alkyl cinnamaldehyde and benzopyran derivatives with excellent E/Z-selectivity.

Palladium-catalyzed carbonylative annulation of terminal alkynes: Synthesis of coumarins and 2-quinolones

o-Iodophenols and o-iodoaniline derivatives react with terminal alkynes under 1 atm of CO in the presence of pyridine and catalytic amounts of Pd(OAc)2 to generate coumarins and 2-quinolones, respectively, as the only products. Terminal alkynes bearing alkyl, aryl, silyl, hydroxyl, ester and cyano substituents are effective in these processes affording the desired products in moderate yields. The formation of coumarins and 2-quinolones in this process is in stark contrast with all previously described palladium-catalyzed reactions of o-iodophenols or o-iodoanilines with terminal alkynes and CO, which have afforded chromones and 4-quinolones. Moreover, under our reaction conditions terminal alkynes insert into the carbon-palladium bond instead of undergoing a Sonogashira-type coupling as confirmed by an isotope labeling experiment.

Reaction of gem-dibromocyclopropanes or iodobenzofuran with trialkylmanganate

Treatment of gem-dibromocyclopropanes with trialkylmanganate, derived from manganese(II) chloride and three equivalents of Grignard reagent or alkyllithium, followed by an addition of electrophiles provided dialkylated cyclopropanes in good yields. It was

Rhodium-catalysed cyclic carbonylation of 2-alkynylphenols: Synthesis of benzofuranones and coumarins

Rhodium-catalysed carbonylation of 2-alkynylphenols 1 under water-gas shift reaction conditions gives benzofuranone derivatives 2 and coumarin derivatives 3 in high yield (up to 96%, 2:3 = 65:35), in which the hydroxy group adjacent to the carbon-carbon triple bond participitates in the cyclic carbonylation.

CARBON-CARBON BOND FORMATION BY THE REACTION OF ORGANOLITHIUMS WITH α-LITHIATED CYCLIC ENOL ETHERS. STEREOSELECTIVE SYNTHESIS OF β- AND γ-HYDROXY DI- AND TRISUBSTITUTED ALKENES

α-Lithiation of dihydrofuran, benzofuran, and dihydropyran followed by treatment with various organolithiums stereoselectively produces in good yields the corresponding ring-opened (E)-alkenyllithiums, i. e., (E)-β(or γ)-hydroxy-ω-alkenyl-ω-lithioalkenes, the lithium atom of which can be readily replaced with H, D, or C groups, such as CO2 or Me.