314284-69-0Relevant articles and documents
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.
Rh(i)-Catalyzed regioselective arylcarboxylation of acrylamides with arylboronic acids and CO2
Cai, Lei,Fu, Lei,Gao, Yuzhen,Li, Gang,Li, Shangda,Zhou, Chunlin
supporting information, p. 7328 - 7332 (2020/11/19)
The first Rh(i)-catalyzed regioselective arylcarboxylation of electron-deficient acrylamides with arylboronic acids under atmospheric pressure of CO2 has been developed. A range of acrylamides and arylboronic acids were compatible with this reaction under redox-neutral conditions, leading to a series of malonate derivatives that are versatile building blocks in organic syntheses.
Manganese-Mediated Reductive Transamidation of Tertiary Amides with Nitroarenes
Cheung, Chi Wai,Ma, Jun-An,Hu, Xile
supporting information, p. 6789 - 6792 (2018/05/29)
Amides are an important class of organic compounds, which have widespread industrial applications. Transamidation of amides is a convenient method to generate new amides from existing ones. Tertiary amides, however, are challenging substrates for transamidation. Here we describe an unconventional approach to the transamidation of tertiary amides using nitroarenes as the nitrogen source under reductive conditions. Manganese metal alone mediates the reactions and no additional catalyst is required. The method exhibits broad scope and high functional group tolerance.
Rhodium-Catalyzed Asymmetric Synthesis of β-Branched Amides
Wu, Zhao,Laffoon, Joshua D.,Nguyen, Trang T.,McAlpin, Jacob D.,Hull, Kami L.
supporting information, p. 1371 - 1375 (2017/01/24)
A general asymmetric route for the one-step synthesis of chiral β-branched amides is reported through the highly enantioselective isomerization of allylamines, followed by enamine exchange, and subsequent oxidation. The enamine exchange allows for a rapid and modular synthesis of various amides, including challenging β-diaryl and β-cyclic.
Rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes: Effective conversion of amines and anilines into amides
Wu, Zhao,Hull, Kami L.
, p. 969 - 975 (2016/02/05)
The rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes is reported. In situ generated [(BINAP)Rh]BF4 catalyzes the one-pot isomerization/oxidative amidation of allylic alcohols or direct amidation of aldehydes using acetone or styrene as the hydrogen acceptor. The conditions are general, affording good to excellent yields with a wide array of amine and aniline nucleophiles, and chemoselective, other alcohols do not participate in the oxidation reaction. Utilization of biphasic conditions is critical, as they promote an equilibrium between the imine/enamine byproducts and the hemiaminal, which can undergo oxidation to the amide.
