908520-36-5

Upstream product

• 578-66-5 8-amino quinoline 
• 17380-62-0 1-phenylcyclopentanecarboxylic acid chloride 
• 77-55-4 1-phenyl-1-cyclopentanecarboxylic acid 

Downstream Products

• 1534433-49-2 2-(4-methoxyphenyl)-1-phenyl-N-(quinolin-8-yl)cyclopentanecarboxamide 
• 1534433-50-5 2,5-bis(4-methoxyphenyl)-1-phenyl-N-(quinolin-8-yl)cyclopentanecarboxamide 
• 77-55-4 1-phenyl-1-cyclopentanecarboxylic acid 
• 5296-89-9 1-phenylcyclopentane-1-carboxamide 

Relevant academic research and scientific papers

Bridging C?H Activation: Mild and Versatile Cleavage of the 8-Aminoquinoline Directing Group

8-Aminoquinoline has emerged as one of the most powerful bidentate directing groups in history of C?H activation within the last decade. However, cleavage of its robust amide bond has shown to be challenging in several cases, thus jeopardizing the general synthetic utility of the method. To overcome this limitation, we herein report a simple oxidative deprotection protocol. This transformation rapidly converts the robust amide to a labile imide, allowing subsequent cleavage in a simple one-pot fashion to rapidly access carboxylic acids or amides as final products.

Palladium-Catalyzed Migratory Insertion of Carbenes and C-C Cleavage of Cycloalkanecarboxamides

A palladium catalyzed reaction of cycloalkanecarboxamides and diazomalonates or bis(phenylsulfonyl)diazomethane has been developed. The reaction proceeds via carbene migratory insertion and cascade C-C cleavage pathways. Cycloalkanecarboxamides with four to seven membered rings are applicable in the transformation. A series of ring opening products were prepared with moderate yields. The finding provides valuable clues for the development of new reactions involving carbene migratory insertion and the cleavage of unstrained C(sp3)-C(sp3) bonds.

Nickel-catalyzed direct arylation of C(sp3)-H bonds in aliphatic amides via bidentate-chelation assistance

The Ni-catalyzed, direct arylation of C(sp3)-H (methyl and methylene) bonds in aliphatic amides containing an 8-aminoquinoline moiety as a bidentate directing group with aryl halides is described. Deuterium-labeling experiments indicate that the C-H bond cleavage step is fast and reversible. Various nickel complexes including both Ni(II) and Ni(0) show a high catalytic activity. The results of a series of mechanistic experiments indicate that the catalytic reaction does not proceed through a Ni(0)/Ni(II) catalytic cycle, but probably through a Ni(II)/Ni(IV) catalytic cycle.