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可回收的铜/碳氮复合材料催化α-羟基酸/炔丙醇偶联反应合成炔丙胺。

Recyclable Cu/CN composite catalyzed AHA/A coupling reactions for the synthesis of propargylamines.

作者信息

Xu Hang, Wang Jun, Wang Peng, Niu Xiyu, Luo Yidan, Zhu Li, Yao Xiaoquan

机构信息

Department of Applied Chemistry, School of Material Science and Technology, Nanjing University of Aeronautics and Astronautics Nanjing 210016 PR China

Department of Chemistry, School of Pharmacy, Nanjing Medical University Nanjing 211166 PR China.

出版信息

RSC Adv. 2018 Sep 24;8(57):32942-32947. doi: 10.1039/c8ra06613b. eCollection 2018 Sep 18.

DOI:10.1039/c8ra06613b
PMID:35547691
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9086382/
Abstract

The heterogeneous Cu/CN catalyst was found to be efficient for the synthesis of propargylamines using a three-component coupling reaction of alkynes, CHCl and amines (AHA) without additional base. Moreover, the catalyst also showed highly catalytic activity in the synthesis of C1-alkynylated tetrahydroisoquinolines (THIQs) an A reaction of alkynes, aldehydes and THIQ. The Cu/CN-catalyzed multicomponent reactions exhibited good functional group tolerance in most examples. Furthermore, the easily prepared Cu/CN catalyst could be recovered and reused conveniently over 5 times without losing catalytic activities.

摘要

研究发现,非均相Cu/CN催化剂可在无额外碱的条件下,通过炔烃、CHCl和胺的三组分偶联反应(AHA)高效合成炔丙胺。此外,该催化剂在炔烃、醛和四氢异喹啉(THIQ)的反应中合成C1-炔基化四氢异喹啉(THIQs)时也表现出高催化活性。在大多数实例中,Cu/CN催化的多组分反应表现出良好的官能团耐受性。此外,易于制备的Cu/CN催化剂可方便地回收和重复使用5次以上而不丧失催化活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65e0/9086382/9a503e0ff595/c8ra06613b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65e0/9086382/47446b007573/c8ra06613b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65e0/9086382/1ed09f411eb0/c8ra06613b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65e0/9086382/8f1133c1627f/c8ra06613b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65e0/9086382/9a503e0ff595/c8ra06613b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65e0/9086382/47446b007573/c8ra06613b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65e0/9086382/1ed09f411eb0/c8ra06613b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65e0/9086382/8f1133c1627f/c8ra06613b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/65e0/9086382/9a503e0ff595/c8ra06613b-f2.jpg

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本文引用的文献

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Monatsh Chem. 2017;148(1):91-104. doi: 10.1007/s00706-016-1877-5. Epub 2016 Dec 9.
2
Catalyst-free activation of methylene chloride and alkynes by amines in a three-component coupling reaction to synthesize propargylamines.在三组分偶联反应中,胺对二氯甲烷和炔烃进行无催化剂活化以合成炔丙胺。
Org Biomol Chem. 2014 Sep 14;12(34):6725-9. doi: 10.1039/c4ob00986j.
3
Enantioselective double manipulation of tetrahydroisoquinolines with terminal alkynes and aldehydes under copper(I) catalysis.
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Angew Chem Int Ed Engl. 2014 Jan 3;53(1):277-81. doi: 10.1002/anie.201308699. Epub 2013 Nov 29.
4
Efficient synthesis of propargylamines from terminal alkynes, dichloromethane and tertiary amines over silver catalysts.银催化剂催化末端炔烃、二氯甲烷和叔胺高效合成炔丙胺。
Org Biomol Chem. 2014 Jan 14;12(2):247-50. doi: 10.1039/c3ob41878b.
5
CuI-catalyzed C1-alkynylation of tetrahydroisoquinolines (THIQs) by A3 reaction with tunable iminium ions.铜催化四氢异喹啉(THIQs)通过 A3 反应与可调变亚胺离子的 C1-炔基化反应。
Org Lett. 2013 Dec 6;15(23):5928-31. doi: 10.1021/ol402517e. Epub 2013 Nov 15.
6
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Org Lett. 2013 Mar 1;15(5):1092-5. doi: 10.1021/ol4001153. Epub 2013 Feb 18.
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Angew Chem Int Ed Engl. 2010 Aug 9;49(34):5961-5. doi: 10.1002/anie.201001699.