52986-71-7

Upstream product

• 106275-96-1 4-ethoxy-6-methoxy-1-methyl-1,2,3,4-tetrahydro-isoquinoline 
• 108-05-4 vinyl acetate 
• 96155-57-6 (E)-1-(4-methoxyphenyl)ethanone O-acetyl oxime 
• 52986-70-6 6-methoxyisoquinoline 
• 591767-62-3 6-methoxyisoquinoline 2-oxide 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 96155-57-6 1-(4-methoxyphenyl)ethanone O-acetyl oxime 

Downstream Products

• 140683-35-8 1-methyl-isoquinolin-6-ol 
• 1443754-95-7 N-phenacyl-1-methyl-6-methoxyisoquinolinium bromide 

Relevant academic research and scientific papers

Palladium-Catalyzed Enantioselective C(sp3)-H Arylation of 2-Propyl Azaaryls Enabled by an Amino Acid Ligand

A palladium(II)-catalyzed enantioselective arylation of unbiased secondary C(sp3)-H bonds was developed. The enantioselectivity was controlled by the combination of a pyridyl or isoquinolinyl directing group and an amino acid, N-Boc-2-pentyl proline. A variety of 2-propyl azaaryls and biaryl iodides were employed to provide arylated products in moderate to good yields (up to 82%) with high enantioselectivities (up to 93:7 er). This reaction is a rare example of an amino-acid-enabled enantioselective acyclic methylene C(sp3)-H arylation. Furthermore, the reaction proceeded with high enantioselectivity even on a gram scale, and the product was transformed to a 5,6,7,8-tetrahydroisoquinoline bioactive molecule. Kinetic isotope effect (KIE) experiments indicated that C-H activation is the rate-determining step for the enantioselective C(sp3)-H arylation.

Isoquinoline synthesis by C-H activation/annulation using vinyl acetate as an acetylene equivalent

Vinyl acetate is used as an acetylene equivalent in rhodium(III)-catalysed C-H activation/annulation with aryl ketoxime esters. Extension to an aldoxime ester allows for a concise formal synthesis of decumbenine B.

Rh-catalyzed sequential oxidative C-H activation/annulation with geminal-substituted vinyl acetates to access isoquinolines

The concise synthesis of 3-substituted or non-C3-substituted isoquinolines through Rh-catalyzed sequential oxidative C-H activation/annulation with geminal-substituted vinyl acetates was developed with good functional group tolerance. The protocol was successfully applied to the total synthesis of the natural product papaverine.