Publication

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

Liu, Y., Afanasenko, A., Elangovan, S., Sun, Z. & Barta, K., 1-Jul-2019, In : ACS Sustainable Chemistry & Engineering . 7, 13, p. 11267-11274 8 p.

Research output: Contribution to journalArticleAcademicpeer-review

APA

Liu, Y., Afanasenko, A., Elangovan, S., Sun, Z., & Barta, K. (2019). Primary Benzylamines by Efficient N-Alkylation of Benzyl Alcohols Using Commercial Ni Catalysts and Easy-to-Handle Ammonia Sources. ACS Sustainable Chemistry & Engineering , 7(13), 11267-11274. https://doi.org/10.1021/acssuschemeng.9b00619

Author

Liu, Yongzhuang ; Afanasenko, Anastasiia ; Elangovan, Saravanakumar ; Sun, Zhuohua ; Barta, Katalin. / Primary Benzylamines by Efficient N-Alkylation of Benzyl Alcohols Using Commercial Ni Catalysts and Easy-to-Handle Ammonia Sources. In: ACS Sustainable Chemistry & Engineering . 2019 ; Vol. 7, No. 13. pp. 11267-11274.

Harvard

Liu, Y, Afanasenko, A, Elangovan, S, Sun, Z & Barta, K 2019, 'Primary Benzylamines by Efficient N-Alkylation of Benzyl Alcohols Using Commercial Ni Catalysts and Easy-to-Handle Ammonia Sources', ACS Sustainable Chemistry & Engineering , vol. 7, no. 13, pp. 11267-11274. https://doi.org/10.1021/acssuschemeng.9b00619

Standard

Primary Benzylamines by Efficient N-Alkylation of Benzyl Alcohols Using Commercial Ni Catalysts and Easy-to-Handle Ammonia Sources. / Liu, Yongzhuang; Afanasenko, Anastasiia; Elangovan, Saravanakumar; Sun, Zhuohua; Barta, Katalin.

In: ACS Sustainable Chemistry & Engineering , Vol. 7, No. 13, 01.07.2019, p. 11267-11274.

Research output: Contribution to journalArticleAcademicpeer-review

Vancouver

Liu Y, Afanasenko A, Elangovan S, Sun Z, Barta K. Primary Benzylamines by Efficient N-Alkylation of Benzyl Alcohols Using Commercial Ni Catalysts and Easy-to-Handle Ammonia Sources. ACS Sustainable Chemistry & Engineering . 2019 Jul 1;7(13):11267-11274. https://doi.org/10.1021/acssuschemeng.9b00619


BibTeX

@article{b5d1f4acc3da4ddf87f72a7cb0e2534d,
title = "Primary Benzylamines by Efficient N-Alkylation of Benzyl Alcohols Using Commercial Ni Catalysts and Easy-to-Handle Ammonia Sources",
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.",
author = "Yongzhuang Liu and Anastasiia Afanasenko and Saravanakumar Elangovan and Zhuohua Sun and Katalin Barta",
year = "2019",
month = "7",
day = "1",
doi = "10.1021/acssuschemeng.9b00619",
language = "English",
volume = "7",
pages = "11267--11274",
journal = "ACS Sustainable Chemistry & Engineering",
issn = "2168-0485",
publisher = "AMER CHEMICAL SOC",
number = "13",

}

RIS

TY - JOUR

T1 - Primary Benzylamines by Efficient N-Alkylation of Benzyl Alcohols Using Commercial Ni Catalysts and Easy-to-Handle Ammonia Sources

AU - Liu, Yongzhuang

AU - Afanasenko, Anastasiia

AU - Elangovan, Saravanakumar

AU - Sun, Zhuohua

AU - Barta, Katalin

PY - 2019/7/1

Y1 - 2019/7/1

N2 - 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.

AB - 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.

U2 - 10.1021/acssuschemeng.9b00619

DO - 10.1021/acssuschemeng.9b00619

M3 - Article

VL - 7

SP - 11267

EP - 11274

JO - ACS Sustainable Chemistry & Engineering

JF - ACS Sustainable Chemistry & Engineering

SN - 2168-0485

IS - 13

ER -

ID: 91887149