Efficient C—N Formation for Preparing α-Branched Primary Amines by Recycled Intramolecular Reactions of 1,8-Naphthosultone Using Ammonia as Nitrogen Source

doi:10.1016/S1004-9541(14)60037-9

Chin.J.Chem.Eng. ›› 2014, Vol. 22 ›› Issue (4): 405-410.DOI: 10.1016/S1004-9541(14)60037-9

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Efficient C—N Formation for Preparing α-Branched Primary Amines by Recycled Intramolecular Reactions of 1,8-Naphthosultone Using Ammonia as Nitrogen Source

ZHOU Xinrui¹, CHEN Jie¹, ZENG Xiaoping¹, LIU Jihong¹, Istvan E. Markó^1,2

1 State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China;
2 Laboratory of Organic and Medicinal Chemistry, Université catholique de Louvain, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium

Received:2012-09-03 Revised:2013-02-18 Online:2014-04-04 Published:2014-04-28
Supported by:
Supported by the National Natural Science Foundation of China (21076036).

Efficient C—N Formation for Preparing α-Branched Primary Amines by Recycled Intramolecular Reactions of 1,8-Naphthosultone Using Ammonia as Nitrogen Source

周新锐¹, 陈洁¹, 曾小萍¹, 刘季红¹, Istvan E. Markó^1,2

1 State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China;
2 Laboratory of Organic and Medicinal Chemistry, Université catholique de Louvain, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium

通讯作者: ZHOU Xinrui, Istvan E. Markó
基金资助:
Supported by the National Natural Science Foundation of China (21076036).

Abstract

Abstract: Amination of tertiary and secondary alcohols using aqueous ammonia as nitrogen source was carried out by a process with recyclable intramolecular reaction of 1,8-naphthosultone, which lead to α-branched primary amines. Sulfonic resin serves as the heterogeneous catalyst for C—N bond formation and protects the neighboring hydroxyl group until the required hydrolysis starts in the alkaline solution. The process can be conducted under mild conditions, no additional solvent is needed and no overreaction to secondary or tertiary amines occurs.

Key words: &, alpha, -branched primary amine, 1,8-naphthosultone, ammonia

摘要： Amination of tertiary and secondary alcohols using aqueous ammonia as nitrogen source was carried out by a process with recyclable intramolecular reaction of 1,8-naphthosultone, which lead to α-branched primary amines. Sulfonic resin serves as the heterogeneous catalyst for C—N bond formation and protects the neighboring hydroxyl group until the required hydrolysis starts in the alkaline solution. The process can be conducted under mild conditions, no additional solvent is needed and no overreaction to secondary or tertiary amines occurs.

关键词: &, alpha, -branched primary amine, 1,8-naphthosultone, ammonia

ZHOU Xinrui, CHEN Jie, ZENG Xiaoping, LIU Jihong, Istvan E. Markó. Efficient C—N Formation for Preparing α-Branched Primary Amines by Recycled Intramolecular Reactions of 1,8-Naphthosultone Using Ammonia as Nitrogen Source[J]. Chin.J.Chem.Eng., 2014, 22(4): 405-410.

周新锐, 陈洁, 曾小萍, 刘季红, Istvan E. Markó. Efficient C—N Formation for Preparing α-Branched Primary Amines by Recycled Intramolecular Reactions of 1,8-Naphthosultone Using Ammonia as Nitrogen Source[J]. Chinese Journal of Chemical Engineering, 2014, 22(4): 405-410.

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Efficient C—N Formation for Preparing α-Branched Primary Amines by Recycled Intramolecular Reactions of 1,8-Naphthosultone Using Ammonia as Nitrogen Source

Efficient C—N Formation for Preparing α-Branched Primary Amines by Recycled Intramolecular Reactions of 1,8-Naphthosultone Using Ammonia as Nitrogen Source

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