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

Jannik C. Borghs; Yury Lebedev; Magnus Rueping; Osama El-Sepelgy

doi:10.1021/acs.orglett.8b03506

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

Jannik C. Borghs, Yury Lebedev, Magnus Rueping, Osama El-Sepelgy

Research output: Contribution to journal › Article › peer-review

61 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	70-74
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.8b03506
State	Published - Dec 24 2018

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: J.C.B. is thankful for financial support of the German Federal Environmental Foundation (DBU).

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10.1021/acs.orglett.8b03506

https://repository.kaust.edu.sa/bitstream/10754/630913/1/manuscript-.pdf

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

abstract = "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.",

author = "Borghs, {Jannik C.} and Yury Lebedev and Magnus Rueping and Osama El-Sepelgy",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: J.C.B. is thankful for financial support of the German Federal Environmental Foundation (DBU).",

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AU - Borghs, Jannik C.

AU - Lebedev, Yury

AU - Rueping, Magnus

AU - El-Sepelgy, Osama

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: J.C.B. is thankful for financial support of the German Federal Environmental Foundation (DBU).

PY - 2018/12/24

Y1 - 2018/12/24

N2 - 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.

AB - 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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JO - Organic Letters

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

Abstract

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CCDC 1863450: Experimental Crystal Structure Determination : bromo-(dicarbonyl)-{2-(diphenylphosphanyl)-N-[2-(diphenylphosphanyl)ethyl]ethan-1-amine}-manganese

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

Abstract

Bibliographical note

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Datasets

CCDC 1863450: Experimental Crystal Structure Determination : bromo-(dicarbonyl)-{2-(diphenylphosphanyl)-N-[2-(diphenylphosphanyl)ethyl]ethan-1-amine}-manganese

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