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Updated: Sep 17, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Nickel-Catalyzed Reductive Coupling: A Practical Approach for the Synthesis of Aryl-Substituted 1,3-Cyclobutanes in
Lorena Rico1, Zachary G Brill1, Samantha A Burgess2
1Department of Discovery Chemistry, Merck & Co., Inc., Boston, Massachusetts 02115, United States.
Abstract:
The synthesis of complex medicinal chemistry scaffolds remains a challenge when developing new methodologies. Here, we describe efficient nickel-catalyzed reductive coupling conditions for synthesizing aryl-substituted 1,3-cyclobutanes, utilizing a highly functionalized alkyl halide and a diverse array of aryl bromides, including sterically hindered ones. We studied the influence of ligand and alkyl halide selection on the reaction efficiency. In addition, we report the use of these conditions on a 12 mmol scale. This work enabled access to a series of adenosine 2A/2B dual receptor antagonists.
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