A mild copper catalyzed method for the selective deprotection of aryl allyl ethers

Abstract

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Nickel-Catalyzed Removal of Alkene Protecting Group of Phenols, Alcohols via Chain Walking Process

“…It means the coordination of the nickel catalyst of the substrate was necessary. Second, ((2,2-dimethylbut-3-en-1-yl)oxy)benzene (9) was subjected to optimal condition, similarly no desire product was observed (3), which means the chain walking was intercepted with the quaternary carbon to stop the formation of key allyl ether. When we analyzed the byproduct of the reaction 3j by GC-MS, the borylated alkene 10 was not detected which means the reaction might not be initiated by Ni-Bpin.…”

“…The most conventional masking of phenols and alcohols are allylethers derived from facile base-promoted substitution of allyl halides [2]. Meanwhile, allylethers are easily removed under acidic, basic, reductive, or oxidative conditions with or without the aid of transition metals (Scheme 1a) [3][4][5][6][7][8][9][10][11]. On the other hand, it means allylethers are not stable in these conditions which diminished its usage in application.…”

Iodine‐DMSO catalyzed chemoselective oxidative aromatization and deallylation, nondeallylation of aryl allyl ether of tetrahydro‐β‐carboline

“…[13] The copper boryl reagents enable the selective cleavage of aryl allyl ethers and selective nondeprotection of allyl ester, but such transformation needed reaction activator. [14] Therefore, it is desirable to develop new methodologies that afford high yielding with nondeallylation and oxidative aromatization/dehydrogenation will occur under mild reaction conditions. β-carbolines are important heterocyclic compounds with a wide range of biological activity [15] (Figure 1).…”