Development of Catalytic Aminoboration of Alkenes

2015 Fiscal Year Final Research Report

• Project/Area Number: 25620084
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Osaka University
• Principal Investigator: Hirano Koji 大阪大学, 工学(系)研究科(研究院), 准教授 (70532696)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: アミノホウ素化 / ヒドロアミノ化 / 求電子的アミノ化 / アミン / アルケン / 有機ホウ素化合物 / 触媒的不斉合成 / 位置選択性

Outline of Final Research Achievements

We have developed copper-catalyzed regio-and stereoselective aminoborations of alkenes by using an electrophilic amination as a key step. Under optimal conditions, electronically activated styrenes as well as strained methylenecyclopropanes and bicyclic alkenes could be employed. Additionally, we successfully found an efficient Cu-based catalyst system for the challenging unactivated terminal alkenes, which are know to be feedstock materials. The obtained aminoboration products can be useful intermediates in organic synthesis because the resulting boron functionality can be a versatile synthetic handle for further transformation. Additionally, related regio- and enantioselective hydroamination catalysis was also developed.

Free Research Field

有機合成化学