Primary Benzylamines by Efficient N-Alkylation of Benzyl Alcohols Using Commercial Ni Catalysts and Easy-to-Handle Ammonia Sources

Release time:2019-05-31 Hits:

Impact Factor:7.1

DOI number:10.1021/acssuschemeng.9b00619

Affiliation of Author(s):格罗宁根大学

Journal:ACS Sustainable Chemistry & Engineering

Abstract:Primary benzylamines are highly important building blocks in the pharmaceutical and polymer industry. An attractive catalytic approach to access these compounds is the direct coupling of benzyl alcohols with ammonia via the borrowing hydrogen methodology. However, this approach is usually hampered by a series of side-reactions, one of the most prominent being the overalkylation of the formed primary amine. Herein, we describe a robust catalytic methodology, which utilizes commercially available heterogeneous Ni catalysts and easy-to-handle ammonia sources, such as aqueous ammonia or ammonium salts, for the formation of primary benzylamines with good selectivity and scope. Notably, our method enables the conversion of potentially lignin-derived vanillyl alcohol to vanillylamine, which can be used to produce emerging biobased polymers or as pharma building blocks. Important sugar derived platform alcohols as well as long chain aliphatic primary alcohols can be successfully aminated. Moreover, we provide an alternative, sustainable route to p-xylylenediamine and m-xylylenediamine, important components of heat resistant polyamides such as Kevlar.

Co-author:Anastasiia Afanasenko,Saravanakumar Elangovan,Zhuohua Sun

First Author:Yongzhuang Liu

Indexed by:Journal paper

Correspondence Author:Katalin Barta

Document Type:J

Volume:7

Issue:13

Page Number:11267-11274

Translation or Not:no

Date of Publication:2019-01-01

Included Journals:SCI

Links to published journals:https://pubs-acs-org-443.webvpn.nefu.edu.cn/doi/10.1021/acssuschemeng.9b00619