1111441-33-8

Upstream product

• 578-66-5 8-amino quinoline 
• 90-27-7 2-Phenylbutyric acid 
• 36854-57-6 2-Phenylbutyryl chloride 

Relevant academic research and scientific papers

Copper catalysed amidation of aryl halides through chelation assistance

A copper mediated C-N bond formation for the amidation of aryl halides using 8-aminoquinoline has been developed. This strategy provides efficient access to amides bearing two contiguous heterocyclic moieties and does not require the presence of additiona

Bidentate ligand 8-aminoquinoline-aided Pd-catalyzed diastereoselective β-arylation of the prochiral secondary sp3 C-H bonds of 2-phenylbutanamides and related aliphatic carboxamides

Investigations on the Pd-catalyzed 8-aminoquinoline-aided diastereoselective β-arylation of the prochiral 2° sp3 C-H bonds of various aliphatic carboxamides having substituents at the α- or γ-positions are reported. The Pd-catalyzed β-arylation of the 2° sp3 C-H bonds of racemic 2-phenylbutanamides with aryl iodides gave the arylated products (±)-3a-l (anti isomers) with moderate to good diastereoselectivities (dr up to 86:14). Next, the Pd-catalyzed β-arylation of various γ-substituted aliphatic carboxamides with aryl iodides furnished the corresponding C-H arylated products with poor diastereoselectivities. Then, the arylation of the C(β)-H bonds of 2-ethyl-N-(quinolin-8-yl)butanamide possessing two prochiral centers with aryl iodides successfully furnished the bis arylated products meso-8eA-hA and (±)-8eB-hB (diastereomers). The arylation of (S)-2-phenylbutanamide also gave the corresponding enantiomerically enriched compounds 10a-c (anti isomers). The stereochemistry of the products (±)-3a-l (major isomers), meso-8eA-hA (major isomers), (±)-8eB-hB (minor isomers) and enantiomerically enriched compounds 10a-c (major isomers) were assigned based on the X-ray structures of the major isomers 3b,c,e,l, 8eA, 10c and minor isomers 8eB and 8fB. The limitations and outcome of the stereocontrol in the Pd-catalyzed C-H arylation reactions involving aliphatic carboxamides are illustrated.

A Two-Step Procedure for the Overall Transamidation of 8-Aminoquinoline Amides Proceeding via the Intermediate N -Acyl-Boc-Carbamates

Herein a two-step strategy for achieving overall transamidation of 8-aminoquinoline amides has been explored. In this protocol, the 8-aminoquinoline amides were first treated with Boc2O and DMAP to form the corresponding N-acyl-Boc-carbamates,

Ag1Pd1 Nanoparticles–Reduced Graphene Oxide as a Highly Efficient and Recyclable Catalyst for Direct Aryl C?H Olefination

The efficient and selective palladium-catalyzed activation of C?H bonds is of great importance for the construction of diverse bioactive molecules. Despite significant progress, the inability to recycle palladium catalysts and the need for additives imped

Palladium-catalyzed aryl C-H olefination with unactivated, aliphatic alkenes

Palladium-catalyzed coupling between aryl halides and alkenes (Mizoroki-Heck reaction) is one of the most popular reactions for synthesizing complex organic molecules. The limited availability, problematic synthesis, and higher cost of aryl halide precursors (or their equivalents) have encouraged exploration of direct olefination of aryl carbon-hydrogen (C-H) bonds (Fujiwara-Moritani reaction). Despite significant progress, the restricted substrate scope, in particular noncompliance of unactivated aliphatic olefins, has discouraged the use of this greener alternative. Overcoming this serious limitation, we report here a palladium-catalyzed chelation-assisted ortho C-H bond olefination of phenylacetic acid derivatives with unactivated, aliphatic alkenes in good to excellent yields with high regio- and stereoselectivities. The versatility of this operationally simple method has been demonstrated through drug diversification and sequential C-H olefination for synthesizing divinylbenzene derivatives.