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铜催化邻氰基苯基丙炔碳酸酯的硼化环化反应:官能化 1-萘胺的合成。

Copper-Catalyzed Borylative Cyclization of o-(Cyano)phenyl Propargyl Carbonates: Synthesis of Functionalized 1-Naphthylamines.

机构信息

State 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.

出版信息

Org Lett. 2018 Jun 15;20(12):3661-3665. doi: 10.1021/acs.orglett.8b01457. Epub 2018 Jun 4.

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.

摘要

邻氰苯基丙炔碳酸酯的铜催化硼酰化环化反应高效高区域选择性地合成了 3-硼基-1-萘胺。该反应提出了通过硼铜化、脱硼、硼铜化和环化形成烯丙基硼酸酯的级联序列。所得产物可通过氧化或金属催化偶联反应进一步合成各种功能化的 1-萘胺。

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