14548-54-0Relevant academic research and scientific papers
Manganese(I) Catalyzed α-Alkenylation of Amides Using Alcohols with Liberation of Hydrogen and Water
Pandia, Biplab Keshari,Gunanathan, Chidambaram
, p. 9994 - 10005 (2021/07/31)
Herein, unprecedented manganese-catalyzed direct α-alkenylation of amides using alcohols is reported. Aryl amides are reacted with diverse primary alcohols, which provided the α,β-unsaturated amides in moderate to good yields with excellent selectivity. Mechanistic studies indicate that Mn(I) catalyst oxidizes the alcohols to their corresponding aldehydes and also plays an important role in efficient C═C bond formation through aldol condensation. This selective olefination is facilitated by metal-ligand cooperation by the aromatization-dearomatization process operating in the catalytic system. Biorenewable alcohols are used as alkenylation reagents for the challenging α-alkenylation of amides with the highly abundant base metal manganese as a catalyst, which results in water and dihydrogen as the only byproduct, making this catalytic transformation attractive, sustainable, and environmentally benign.
Synthesis of Linear α,β-Unsaturated Amides from Isocyanates and Alkenylaluminum Reagents
Chen, Bo,Wu, Xiao-Feng
supporting information, p. 788 - 792 (2020/05/19)
A new approach has been developed for the synthesis of linear α,β-unsaturated amides by the direct coupling of isocyanates with alkenylaluminum reagents. At room temperature, the desired α,β-unsaturated amides were isolated in good to excellent yields with good functional-group tolerance in the absence of any catalyst or additive.
Palladium-catalyzed carbonylative synthesis of α,β-unsaturated amides from aryl azides and alkenylaluminum reagent
Chen, Bo,Wu, Xiao-Feng
, p. 160 - 163 (2020/02/11)
In this work, an interesting procedure for the synthesis of α,β-unsaturated amides from aryl azides and alkenylaluminum reagent has been developed. With palladium as the catalyst and XPhos as the ligand under carbon monoxide pressure, the desired α,β-unsaturated amides were isolated in good to excellent yields with good functional group tolerance. Remarkably, this procedure also represents an example on addition of organometallic reagent to isocyanates for α,β-unsaturated amides synthesis.
Direct transformation of arylpropynes to acrylamides via a three-step tandem reaction
Qiu, Jun,Zhang, Ronghua
supporting information, p. 1556 - 1560 (2014/03/21)
A novel and metal-free acrylamides formation between arylpropynes and hydroxylamine hydrochloride through sp3 C-H and C-C bond cleavage has been achieved with DDQ as an oxidant. The mechanistic study shows that the acrylamides are formed through a three-step tandem sequence, including cross-dehydrogenative-coupling (CDC) reaction, aza-Meyer-Schuster rearrangement and Beckmann rearrangement. This journal is The Royal Society of Chemistry 2014.
DDQ-promoted direct transformation of benzyl hydrocarbons to amides via tandem reaction of the CDC reaction and Beckmann rearrangement
Qiu, Jun,Zhang, Ronghua
supporting information, p. 6008 - 6012 (2013/09/12)
An atom-efficient and transition metal-free approach to amides from the corresponding benzyl hydrocarbons through C-H and C-C bond cleavage has been developed. Mechanistic studies have shown that a DDQ-promoted cross-dehydrogenative coupling (CDC) reaction with subsequent oxidation and rearrangement are involved in this transformation. The Royal Society of Chemistry.
