Copper-Catalyzed Borylative Cyclization of o-(Cyano)phenyl Propargyl Carbonates: Synthesis of Functionalized
Meijun Xiong1, Hui Hu1, Xiaoping Hu1
1State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry , University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Lu , Shanghai 200032 , People's Republic of China.
Abstract:
Copper-catalyzed borylative cyclization of o-(cyano)phenyl propargyl carbonates leads to a highly efficient and regioselective synthesis of 3-boryl-1-naphthylamines. A cascade sequence involving the formation of allenyl boronates via borylcupration, deborylation, borylcupration, and cyclization is proposed for this reaction. The resulting products have been applied for the synthesis of a variety of functionalized 1-naphthylamines via oxidation or metal-catalyzed coupling reactions.
More Related Videos
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Related Concept Videos
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Synthesis and Functions of Calcitonin
The exact mechanisms by which calcitonin operates in calcium homeostasis remain elusive, but its significance is evident in several vital...
Transfer RNA Synthesis
Each of these chemical modifications is carried by a specific enzyme, post-transcription. All of these enzymes have unique base and site-specificity. Methylation, the most common chemical modification, is carried by at least nine different enzymes, with...
The Carbon Cycle
Carbon Skeletons
