Development of environmental load-reducing oxidation reactions involving anti-Markovnikov nucleophilic attack to alkenes as a key step

2015 Fiscal Year Final Research Report

• Project/Area Number: 25410116
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Nara Women's University
• Principal Investigator: Ura Yasuyuki 奈良女子大学, 自然科学系, 准教授 (40335196)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: 環境低負荷型酸化反応 / アルケン / 逆マルコフニコフ求核攻撃 / アルデヒド合成 / パラジウム触媒 / 分子状酸素 / 末端アセタール合成 / 酸化的開裂

Outline of Final Research Achievements

We have developed three types of oxidation reactions, i.e., (1) synthesis of arylacetaldehydes via anti-Markovnikov Wacker-type oxidation, (2) synthesis of terminal acetals, (3) synthesis of benzaldehydes via oxidative cleavage of carbon-carbon double bond, using palladium catalysts and vinylarenes as substrates. These reactions proceeded under 1 atm of molecular oxygen (as a terminal oxidant) and mild reaction conditions, and thus these can be regarded as novel environmental load-reducing synthesis of aldehydes and their derivatives from terminal alkenes. The use of cyclic electron-deficient alkenes such as maleimide as additives was the key of the present reactions to enhance the catalytic activity.

Free Research Field

有機金属化学