867347-49-7

Upstream product

• 578-66-5 8-amino quinoline 
• 645-45-4 hydrocinnamic acid chloride 
• 501-52-0 3-Phenylpropionic acid 
• 591-50-4 iodobenzene 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 33757-46-9 8-(N-propionylamino)quinoline 
• 66003-76-7 Diphenyliodonium triflate 

Downstream Products

• 1061490-12-7 3,3-diphenyl-N-(quinolin-8-yl)propanamide 

Relevant academic research and scientific papers

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.

Asymmetric synthesis of β-lactam via palladium-catalyzed enantioselective intramolecular c(sp3)-h amidation

β-Lactams are important scaffolds in drug design and frequently used as reactive intermediates in organic synthesis. Catalytic reactions featuring intramolecular C-H amidation of alkyl carboxamide substrates could provide a straightforward disconnection strategy for β-lactam synthesis. Herein, we report a streamlined method for asymmetric synthesis of β-aryl β-lactams from propanoic acid and aryl iodides via Pd-catalyzed sequential C(sp3)-H functionalization. The lactam-forming reaction provides an example of PdII-catalyzed enantioselective intramolecular C(sp3)-H amidation reaction and proceeds up to 94% ee. The use of a 2-methoxy-5-chlorophenyl iodide oxidant is critical to control the competing reductive elimination pathways of the PdIV intermediate to achieve the desired chemoselectivity. Mechanistic studies suggest that both steric and electronic effects of the unconventional aryl iodide oxidant are responsible for controlling the competing C-N versus C-C reductive elimination pathways of the PdIV intermediate.

Regioselective remote C5 cyanoalkoxylation and cyanoalkylation of 8-aminoquinolines with azobisisobutyronitrile

The efficient regioselective C-H cyanoalkoxylation and cyanoalkylation of 8-aminoquinoline derivatives at the C5 position have been achieved under O2 and N2 atmospheres, respectively. Using 2,2′-azobisisobutyronitrile (AIBN) as a radical precursor, the pr

Tandem Remote Csp3-H Activation/Csp3-Csp3 Cleavage in Unstrained Aliphatic Chains Assisted by Palladium(II)

We report here a proof-of-concept for the cleavage of unstrained remote Csp3-Csp3 bonds at room temperature assisted by a directing group, opening up new possibilities to use aliphatic carboxylic acids as suitable alkenyl coupling partners. This strategy involves the Pd-mediated Csp3-H activation directed by a tethered 8-aminoquinoline group, followed by a concerted asynchronous carbene insertion into the Pd-C bond, and an unexpected β-carbon-carbon bond splitting. The insertion of a coupling partner into a Pd-C bond is a novel route to promote C-C bond cleavage, which in contrast to most common methodologies does not rely on the use of strained carbocycles.

Iron(III)-catalyzed highly regioselective halogenation of 8-amidoquinolines in water

A simple protocol of iron(III)-catalyzed halogenation of 8-amidoquinolines in water under mild conditions was developed, affording the 5-halogenlated products in good to excellent yields up to 98%. The reaction mechanism most likely involves a single-elec

Organic ligand-free carbonylation reactions with unsupported bulk Pd as catalyst

Herein, surprising results for bulk Pd-catalyzed carbonylation reactions are presented. Three types of carbonylation reactions can be realized efficiently under organic ligand-free conditions, namely, hydroaminocarbonylation of olefins, aminocarbonylation of aryl iodides and oxidative carbonylation of amines, which almost cover all the known mechanisms in carbonylation reactions. Notably, the bulk Pd catalyst system exhibited better catalytic activity than the classical homogeneous PdCl2/(2-OMePh)3P catalyst system. This study will create a momentous and new field of green carbonylation reactions.

C5-Regioselective C-H fluorination of 8-aminoquinoline amides and sulfonamides with Selectfluor under metal-free conditions

A novel and efficient regioselective C-H fluorination of 8-aminoquinoline amides and sulfonamides at the C5 position was achieved. Using Selectfluor as a "F" reagent and HOAc as an additive, the reaction proceeds smoothly via a radical pathway. This metho

Palladium-Catalyzed Base-Promoted Arylation of Unactivated C(sp3)–H Bonds by Aryl Iodides: A Practical Approach To Synthesize β-Aryl Carboxylic Acid Derivatives

A highly efficient protocol for the β-arylation of carboxylic amides by aryl iodides under PdCl2(CH3CN)2/CsOAc catalysis was developed. This method was found to tolerate a broad scope of substrates and was successfully employed in the preparation of a variety of β-aryl α-amino and γ-amino acid derivatives. The utility of this method was further illustrated in the synthesis of the psychotropic drug (±)-phenibut and β-aryl bile acid analogues.

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

Detailed mechanistic studies on palladium-catalyzed selective C-H olefination with aliphatic alkenes: A significant influence of proton shuttling

Directing group-assisted regioselective C-H olefination with electronically biased olefins is well studied. However, the incorporation of unactivated olefins has remained largely unsuccessful. A proper mechanistic understanding of olefination involving un