Design and Synthesis of a Novel Primary Amine-Thiourea Organocatalyst Based on Unactivated C(sp3)-H Amination Reaction

In order to apply the C-H activation strategy to the synthesis of novel organic catalysts, a novel primary amine-thiourea catalyst is designed and synthesized by using the developed inert C(sp3)-H amination method as a key step. First, using phenylalanine as the substrate and di-tert-butyl-azodicarb...

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Autores principales:	LIAN Pengfei, WANG Xunhui, ZHANG Shuyu
Formato:	article
Lenguaje:	ZH
Publicado:	Editorial Office of Journal of Shanghai Jiao Tong University 2020
Materias:	c-h amination primary amine thiourea organic catalysis Engineering (General). Civil engineering (General) TA1-2040 Chemical engineering TP155-156 Naval architecture. Shipbuilding. Marine engineering VM1-989
Acceso en línea:	https://doaj.org/article/20eccaf7b61743228e496bc5dd758cb8
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spelling	oai:doaj.org-article:20eccaf7b61743228e496bc5dd758cb82021-11-04T09:34:51ZDesign and Synthesis of a Novel Primary Amine-Thiourea Organocatalyst Based on Unactivated C(sp3)-H Amination Reaction1006-246710.16183/j.cnki.jsjtu.2020.144https://doaj.org/article/20eccaf7b61743228e496bc5dd758cb82020-12-01T00:00:00Zhttp://xuebao.sjtu.edu.cn/CN/10.16183/j.cnki.jsjtu.2020.144https://doaj.org/toc/1006-2467In order to apply the C-H activation strategy to the synthesis of novel organic catalysts, a novel primary amine-thiourea catalyst is designed and synthesized by using the developed inert C(sp3)-H amination method as a key step. First, using phenylalanine as the substrate and di-tert-butyl-azodicarboxylic acid as the nitrogen source, the corresponding amination products are obtained by employing the Pd-catalyzed inert C(sp3)-H amination method. Next, the chiral skeleton of 1,2-diamine privileged in organocatalysts is obtained by simple conversion. Then, a novel chiral primary amine-thiourea bifunctional organic catalyst is synthesized, whose structure is characterized by nuclear magnetic resonance (NMR) and high resolution mass spectrometry (HRMS). The synthesized catalyst is also successfully applied to the asymmetric Michael addition reaction of isobutyraldehyde with nitroolefins. Due to the advantages of transition metal-catalyzed C-H activation, such as simplicity, high efficiency, high atomic economy, and non pre-functionalization, its application to the development of small molecular catalysts will undoubtedly make the structure of catalyst more diversified and the synthesis process more efficient.LIAN PengfeiWANG XunhuiZHANG ShuyuEditorial Office of Journal of Shanghai Jiao Tong Universityarticlec-h aminationprimary aminethioureaorganic catalysisEngineering (General). Civil engineering (General)TA1-2040Chemical engineeringTP155-156Naval architecture. Shipbuilding. Marine engineeringVM1-989ZHShanghai Jiaotong Daxue xuebao, Vol 54, Iss 12, Pp 1335-1339 (2020)
institution	DOAJ
collection	DOAJ
language	ZH
topic	c-h amination primary amine thiourea organic catalysis Engineering (General). Civil engineering (General) TA1-2040 Chemical engineering TP155-156 Naval architecture. Shipbuilding. Marine engineering VM1-989
spellingShingle	c-h amination primary amine thiourea organic catalysis Engineering (General). Civil engineering (General) TA1-2040 Chemical engineering TP155-156 Naval architecture. Shipbuilding. Marine engineering VM1-989 LIAN Pengfei WANG Xunhui ZHANG Shuyu Design and Synthesis of a Novel Primary Amine-Thiourea Organocatalyst Based on Unactivated C(sp3)-H Amination Reaction
description	In order to apply the C-H activation strategy to the synthesis of novel organic catalysts, a novel primary amine-thiourea catalyst is designed and synthesized by using the developed inert C(sp3)-H amination method as a key step. First, using phenylalanine as the substrate and di-tert-butyl-azodicarboxylic acid as the nitrogen source, the corresponding amination products are obtained by employing the Pd-catalyzed inert C(sp3)-H amination method. Next, the chiral skeleton of 1,2-diamine privileged in organocatalysts is obtained by simple conversion. Then, a novel chiral primary amine-thiourea bifunctional organic catalyst is synthesized, whose structure is characterized by nuclear magnetic resonance (NMR) and high resolution mass spectrometry (HRMS). The synthesized catalyst is also successfully applied to the asymmetric Michael addition reaction of isobutyraldehyde with nitroolefins. Due to the advantages of transition metal-catalyzed C-H activation, such as simplicity, high efficiency, high atomic economy, and non pre-functionalization, its application to the development of small molecular catalysts will undoubtedly make the structure of catalyst more diversified and the synthesis process more efficient.
format	article
author	LIAN Pengfei WANG Xunhui ZHANG Shuyu
author_facet	LIAN Pengfei WANG Xunhui ZHANG Shuyu
author_sort	LIAN Pengfei
title	Design and Synthesis of a Novel Primary Amine-Thiourea Organocatalyst Based on Unactivated C(sp3)-H Amination Reaction
title_short	Design and Synthesis of a Novel Primary Amine-Thiourea Organocatalyst Based on Unactivated C(sp3)-H Amination Reaction
title_full	Design and Synthesis of a Novel Primary Amine-Thiourea Organocatalyst Based on Unactivated C(sp3)-H Amination Reaction
title_fullStr	Design and Synthesis of a Novel Primary Amine-Thiourea Organocatalyst Based on Unactivated C(sp3)-H Amination Reaction
title_full_unstemmed	Design and Synthesis of a Novel Primary Amine-Thiourea Organocatalyst Based on Unactivated C(sp3)-H Amination Reaction
title_sort	design and synthesis of a novel primary amine-thiourea organocatalyst based on unactivated c(sp3)-h amination reaction
publisher	Editorial Office of Journal of Shanghai Jiao Tong University
publishDate	2020
url	https://doaj.org/article/20eccaf7b61743228e496bc5dd758cb8
work_keys_str_mv	AT lianpengfei designandsynthesisofanovelprimaryaminethioureaorganocatalystbasedonunactivatedcsp3haminationreaction AT wangxunhui designandsynthesisofanovelprimaryaminethioureaorganocatalystbasedonunactivatedcsp3haminationreaction AT zhangshuyu designandsynthesisofanovelprimaryaminethioureaorganocatalystbasedonunactivatedcsp3haminationreaction
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Design and Synthesis of a Novel Primary Amine-Thiourea Organocatalyst Based on Unactivated C(sp3)-H Amination Reaction

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