138487-22-6

Upstream product

• 873-73-4 4-n-chlorophenylacetylene 
• 637-87-6 1-Chloro-4-iodobenzene 
• 5390-04-5 pent-1-yn-5-ol 
• 503-30-0 trimethylene oxide 

Downstream Products

• 873961-37-6 5-(4-chlorophenyl)-4-pentynal 
• 861920-98-1 7-(4-chloro-phenyl)-1-phenyl-hepta-1,6-diyn-3-one 
• 500709-37-5 1-chloro-4-(5-iodopent-1-ynyl)benzene 
• 500709-38-6 5-(4-Chlorophenyl)pent-4-yn-1-ol p-toluenesulfonate 
• 1172131-51-9 5-(4-chlorophenyl)-4-pentynoic acid 
• 1379654-70-2 (Z)-5-(4-chlorophenyl)pent-2-en-4-ynal 
• 1379654-69-9 (E)-5-(4-chlorophenyl)pent-2-en-4-ynal 
• 1620403-87-3 C₂₀H₂₀ClNO₂ 
• 1620403-96-4 C₁₈H₁₈ClNO 
• 1620404-05-8 C₁₈H₁₇ClN₂O₂ 
• 1620404-13-8 C₁₉H₁₆ClNO₂ 
• 1620404-28-5 C₁₈H₁₆ClNO 
• 1620403-72-6 C₁₉H₁₈ClNO₂ 
• 1620403-55-5 C₁₇H₁₆ClNO 

Relevant academic research and scientific papers

Tetrahydroxydiboron-Promoted Radical Addition of Alkynols

Tetrahydroxydiboron has previously been used as a borylation or reducing reagent in organic synthesis. Herein, we present a novel tetrahydroxydiboron-promoted radical addition of internal alkynes followed by intramolecular oxidation of alcohol through 1,5-hydrogen atom transfer. Preliminary mechanistic studies showed that the process might be initiated through N,N-dimethylformamide-assisted homolytic cleavage of tetrahydroxydiboron. This process provides a convenient synthesis of fluoroalkyl-substituted alkenes with a pendant aldehyde or ketone moiety.

Enantioselective nickel-catalyzedanti-arylmetallative cyclizations onto acyclic electron-deficient alkenes

Enantioselective nickel-catalyzed reactions of (hetero)arylboronic acids or alkenylboronic acids with substrates containing an alkyne tethered to various acyclic electron-deficient alkenes are described.

Palladium-Catalyzed Synthesis of Tricyclic Indoles via a N-S Bond Cleavage Strategy

In palladium/norbornene (Pd/NBE) chemistry, the "ortho effect"has been proven to be a key factor in the process of β-carbon elimination to extrude NBE. Herein, we found that the o-iodoaniline protected by a p-methoxybenzenesulfonyl group can recover the "

Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions

The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon. The electronic effects are studied in other contexts, including hydroacyloxylation and hydroamination, and similar trends in directionality are predominant although not uniformly observed.

Palladium/Norbornene-Catalyzed C?H Alkylation/Alkyne Insertion/Indole Dearomatization Domino Reaction: Assembly of Spiroindolenine-Containing Pentacyclic Frameworks

Reported is a highly chemoselective intermolecular annulation of indole-based biaryls with bromoalkyl alkynes by using palladium/norbornene (Pd/NBE) cooperative catalysis. This reaction is realized through a sequence of Catellani-type C?H alkylation, alkyne insertion, and indole dearomatization, by forming two C(sp2)?C(sp3) and one C(sp2)?C(sp2) bonds in a single chemical operation, thus providing a diverse range of pentacyclic molecules, containing a spiroindolenine fragment, in good yields with excellent functional-group tolerance. Preliminary mechanistic studies reveal that C?H bond cleavage is likely involved in the rate-determining step, and the indole dearomatization might take place through an olefin coordination/insertion and β-hydride elimination Heck-type pathway.

Rh(III)-catalyzed intramolecular redox-neutral or oxidative cyclization of alkynes: Short, efficient synthesis of 3,4-fused indole skeletons

A Rh(III)-catalyzed intramolecular redox-neutral or oxidative annulation of a tethered alkyne has been developed to efficiently construct 3,4-fused indoles via a C-H activation pathway. The advantages of this process are (1) ready availability of annulation precursors; (2) broad substrate scope; (3) complete regioselectivity; (4) simple and mild reaction conditions; and (5) no need for an external oxidant or to employ molecular oxygen as the stoichiometric terminal oxidant.

Cycloaddition reactions of 1,3-diazabuta-1,3-dienes with alkynyl ketenes

The cycloaddition reactions of 'all-carbon' 1,3-diazabuta-1,3-dienes with a few conjugated and unconjugated alkynyl ketenes are described. The reactions provide some interesting azetidinones and dihydropyrimidinones bearing an alkynyl moiety. The regiochemistry of cycloadduct is related with the degree of conjugation of the alkynyl ketene. Moreover, two alternative approaches to 'all-carbon' 1,3-diazabuta-1,3-dienes are reported.

The Photo-Dehydro-Diels-Alder (PDDA) reaction - A powerful method for the preparation of biaryls

The photochemically initiated dehydro-Diels-Alder (PDDA) reaction is an efficient and versatile method for the preparation of biaryls. The ring closure may take place both inter- and intramolecularly, of which the intramolecular variant is more productive

The photo-dehydro-diels-alder reaction: An efficient route to naphthalenes

The photo-dehydro-Diels-Alder reaction (PDDA), a new photochemical route to naphthalenes is presented. The [4+2] cycloaddition takes place between 3-arylynones and arylacetylenes. in which these moieties may be located in two molecules (intermolecular PDD