Zn Mediated Regioselective Barbier Reaction of Propargylic Bromides in THF/aq. NH4Cl Solution

Abstract

The reaction of substituted and unsubstituted propargylic bromides with butanal in presence of zinc power in THF/saturated aqueous NH4Cl solution gave corresponding allenic and propargylic alcohols with high selectivity.

AuCl3-catalyzed synthesis of (E/Z)‒chloroallyl carbazoles via a cascade cyclization process

“…The starting materials 1a-t were prepared via the literature. [43][44][45][46] As shown in Table 2, the substrates 1b (R 1 = 4-Tol, R 2 = H) and 1c (R 1 = 4-MeOC6H4, R 2 = H) which have electron-donating groups at the R 1 positions gave the products 2b and 2c in 72 and 76% yields, respectively (Table 2, entries 2 & 3). When the substrate bearing electron-withdrawing group at R 1 position like 1d (R 1 = 4-FC6H4, R 2 = H) gave the product 2d in 71% yield (Table 2, entry 4).…”

Indium‐mediated allylation of carbonyl compounds in deep eutectic solvents

“…The addition of ammonium salts has been reported to have a positive impact on this type of reaction under aqueous conditions. [ 10 ] Therefore, we decided to study the impact of the addition of the ammonium acetate in both choline chloride:ethylene glycol (1:2) and acetylcholine chloride:acetamide (1:2) mixtures. When 28 mol% of ammonium acetate was added, compound 3a was obtained in both mixtures with excellent yields (Entries 11 and 12, footnote c).…”

Synthesis of [6,6,m]-Tricyclic Compounds via [4+2] Cycloaddition with Au or Cu Catalyst

“…NH 4 Cl solution. 25 Based on this, the aldehyde was treated with allenyl bromide and zinc dust in solvent mixture to obtain propargylic alcohol by Barbier reaction. Then, 10a was synthesized through oxidation and acetal deprotection.…”