A Borrowing Hydrogen Strategy for Dehydrative Coupling of Aminoisoquinolines with Benzyl Alcohols in Water was written by Hikawa, Hidemasa;Tan, Rie;Tazawa, Aoi;Kikkawa, Shoko;Azumaya, Isao. And the article was included in European Journal of Organic Chemistry in 2020.COA of Formula: C9H8N2 This article mentions the following:
We report a borrowing hydrogen strategy for a palladium-catalyzed dehydrative coupling of aminoisoquinolines with benzylic alcs. in water. This cascade reaction using the π-benzylpalladium system can be achieved in an atom-economic process without the need for base or other additives, furnishing the N-benzylated aminoisoquinolines in moderate to excellent yields along with water as the sole co-product. The crossover experiment using [D7]benzyl alc. and 4-methoxybenzyl alc. afforded H/D scrambled products. KIE experiments showed that benzylic C-H bond cleavage of benzyl alc. was involved in the turnover limiting step (KIE = 4.4). The coupling reaction was found to be first order in benzyl alc. with a kinetic solvent isotope effect (KSIE) of 1.6. These exptl. results are consistent with a borrowing hydrogen mechanism in water. Notably, the water-soluble Pd0/TPPMS system can be applied to the more challenging catalytic benzylic amination with aminoisoquinoline nucleophiles despite the possible deactivation of PdII species. In the experiment, the researchers used many compounds, for example, Isoquinolin-7-amine (cas: 23707-37-1COA of Formula: C9H8N2).
Isoquinolin-7-amine (cas: 23707-37-1) belongs to isoquinoline derivatives. Quinoline and its derivatives are widely used as fungicides, biological agents, antibiotics, alkaloids, dyes, rubber chemicals and flavoring agents. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.COA of Formula: C9H8N2
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem