608515-45-3

Upstream product

• 360575-28-6 2-bromo-6-fluorobenzaldehyde 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 1075-00-9 8-fluoroisoquinoline 

Relevant academic research and scientific papers

A new and facile approach to 1,2-dihydroisoquinolin-3(4: H)-imines by the Cu(i)-catalyzed reaction of 2-ethynylbenzyl methanesulfonates, sulfonyl azides and amines

A new, step-economical and operationally simple access to unsubstituted 1,2-dihydroisoquinolin-3(4H)-imines by Cu-catalyzed MCRs under mild conditions is described. In addition, selective hydrolysis of imines to the corresponding 1,2-dihydroisoquinolin-3(4H)-ones under refluxed conc. HCl has also been investigated.

Palladium-Catalyzed Aminomethylative Oppolzer-Type Cyclization of Enynes: Access to Aminomethylated Benzofulvenes

A novel palladium-catalyzed Oppolzer-type cyclization reaction aided by the aminomethyl cyclopalladated complex has been developed, which provides rapid access to functionalized benzofulvenes with excellent stereoselectivity. The corresponding products can undergo Diels–Alder reaction with maleimides, providing a series of complex polycyclic compounds with excellent regio- and stereoselectivities.

Catalytic Asymmetric Tandem Cycloisomerization/[5+2] Cycloaddition Reaction of N-Aryl Nitrone Alkynes with Methyleneindolinones

An asymmetric tandem cycloisomerization and intermolecular [5+2] cycloaddition reaction of 2-ethynylphenyl-substituted nitrones with methyleneindolinones was realized. The process includes the palladium(II)-promoted in situ formation of azomethine ylide and the following chiral N,N′-dioxide-Co(II) complex-catalyzed regio-, diastereo-, and enantioselective [5+2] cycloaddition reaction. The desired spiro-tropanyl oxindoles were obtained in good yields with excellent dr and ee values. On the basis of the determination of the catalyst structure, a possible transition state model was proposed.

Palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination: Access to functionalized naphthalenes

A palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination of enyne-tethered allylic alcohols with aminals is described. Under the reaction conditions, the cationic vinyl allylpalladium species undergoes selective migratory insertion of alkenes rather than reductive elimination with nucleophiles. This strategy provides an efficient and unique approach to the construction of functionalized naphthalenes, which are important building blocks in synthetic organic chemistry. Mechanistic studies have revealed that the selective sequential migratory insertion of enyne and alkene is crucial for the cyclization.

Chiral Cyclometalated Oxazoline Gold(III) Complex-Catalyzed Asymmetric Carboalkoxylation of Alkynes

Asymmetric catalysis by using novel chiral O,O′-chelated 4,4′-biphenol cyclometalated oxazoline gold(III) complexes has been developed. A high yield (≤89%) and a high enantioselectivity (≤90% ee) were achieved in asymmetric carboalkoxylation of alkynes. E

De Novo Synthesis of Phenols and Naphthols through Oxidative Cycloaromatization of Dienynes

In this work, a rhodium-catalyzed oxidative cycloaromatization of dienynes, which provides a highly straightforward and efficient way to access polysubstituted naphthols and phenols under mild conditions, is described. Challenged electron-withdrawing groups are well tolerated in this protocol, and late-stage phenyl ring formation is demonstrated.

Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes

1,5-Diyne systems bearing one terminal and one benzyl- or allyl-substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold-catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C(sp2)–H bond of the offered unsaturated systems. If H atoms are present in the propargylic position, a subsequent isomerization to the aromatic system takes place leading to 9H-fluorene and 11H-benzo[b]fluorene derivatives as final products. In the case of a quaternary carbon in the propargylic position no further aromatization is observed and 10H-benzo[b]fluorene derivatives are obtained in high yield. (Figure presented.).

Rhodium(II)-Catalyzed and Thermally Induced Intramolecular Migration of N-Sulfonyl-1,2,3-triazoles: New Approaches to 1,2-Dihydroisoquinolines and 1-Indanones

New rhodium(II)-catalyzed or thermally induced intramolecular alkoxy group migration of N-sulfonyl-1,2,3-triazoles has been developed, affording divergent synthesis of 1,2-dihydroisoquinoline and 1-indanone derivatives according to different conditions. N-Sulfonyl keteneimine is the key intermediate for the synthesis of dihydroisoquinoline, whereas the aza-vinyl carbene intermediate results in the formation of 1-indanone.

Stereoselective Synthesis of Oxabicyclo[2.2.1]heptenes via a Tandem Dirhodium(II)-Catalyzed Triazole Denitrogenation and [3 + 2] Cycloaddition

A novel synthetic strategy for the diastereoselective synthesis of structurally diverse oxabicyclo[2.2.1]heptenes has been developed, featuring a tandem reaction combining a Rh-catalyzed triazole denitrogenation and a novel type of [3 + 2] cycloaddition reaction. This tandem reaction was thought to proceed via a five-membered oxonium ylide intermediate, which was formed by the intramolecular nucleophilic attack of the carbonyl group on the α-imino metallocarbene followed by an inter- or intramolecular [3 + 2] dipolar cycloaddition with a range of alkynes and alkenes.

Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes

A highly enantioselective carboalkoxylation of alkynes catalyzed by cationic (DTBM-MeO-Biphep)gold(I) complexes is reported. Various optically active β-alkoxyindanone derivatives were obtained in good yields with high enantioselectivities. Furthermore, this methodology was extended to the enantioselective synthesis of 3-methoxycyclopentenones. The reaction is proposed to proceed through an enantioselective cyclization of intermediates containing vinylgold(I) and prochiral oxocarbenium moieties.