Sustainable Manganese-Catalyzed Solvent-Free Synthesis of Pyrroles from 1,4-Diols and Primary Amines

被引：66
作者：
Borghs, Jannik C. [1 ]
Lebedev, Yury [2 ]
Rueping, Magnus [1 ,2 ]
El-Sepelgy, Osama [1 ]
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany
[2] KAUST, KCC, Thuwal 239556900, Saudi Arabia
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 01期
关键词：
BORROWING HYDROGEN; N-HETEROCYCLIZATION; ALPHA-ALKYLATION; MULTICOMPONENT SYNTHESIS; SECONDARY ALCOHOLS; COOPERATIVE METAL; IRON CATALYSIS; CYCLIC IMIDES; RUTHENIUM; KETONES;
D O I：
10.1021/acs.orglett.8b03506
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general and selective metal-catalyzed conversion of biomass-derived primary diols and amines to the highly valuable 2,5-unsubstituted pyrroles has been developed. The reaction is catalyzed by a stable nonprecious manganese complex (1 mol %) in the absence of organic solvents whereby water and molecular hydrogen are the only side products. The manganese catalyst shows unprecedented selectivity, avoiding the formation of pyrrolidines, cyclic imides, and lactones.
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收藏
页码：70 / 74
页数：5
相关论文
共 90 条
[41]  
Jang Y. K., 2018, ORG LETT, DOI [10.1021/acs.orglett.8b03184, DOI 10.1021/ACS.ORGL6ETT.8B03184]
[42]  
Jones R. A., 2008, CHEM HETEROCYCLIC 2, V48
[43]  
Jones R. A., 2008, CHEM HETEROCYCLIC 1, V48
[44]  
Jose S., 2015, BIOMASS AND BIOFUELS
[45]  
Joule J.A., 2010, Heterocyclic Chemistry, V5th
[46]   Manganese Complexes for (De)Hydrogenation Catalysis: A Comparison to Cobalt and Iron Catalysts [J].
Kallmeier, Fabian ;
Kempe, Rhett .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (01) :46-60
[47]   Manganese-Catalyzed Sustainable Synthesis of Pyrroles from Alcohols and Amino Alcohols [J].
Kallmeier, Fabian ;
Dudziec, Beata ;
Irrgang, Torsten ;
Kempe, Rhett .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (25) :7261-7265
[48]   Highly Active and Selective Manganese C=O Bond Hydrogenation Catalysts: The Importance of the Multidentate Ligand, the Ancillary Ligands, and the Oxidation State [J].
Kallmeier, Fabian ;
Irrgang, Torsten ;
Dietel, Thomas ;
Kempe, Rhett .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (39) :11806-11809
[49]   Metal-Ligand Cooperation [J].
Khusnutdinova, Julia R. ;
Milstein, David .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (42) :12236-12273
[50]  
Knorr L., 1884, CHEM BER-RECL, V17, P1635, DOI [10.1002/cber.18840170220, DOI 10.1002/CBER.18840170220]
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