Manganese(III) Porphyrin-Catalyzed Dehydrogenation of Alcohols to form Imines, Tertiary Amines and Quinolines

Kobra Azizi, Sedigheh Akrami, Robert Madsen*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Manganese(III) porphyrin chloride complexes have been developed for the first time as catalysts for the acceptorless dehydrogenative coupling of alcohols and amines. The reaction has been applied to the direct synthesis of imines, tertiary amines and quinolines where only hydrogen gas and/or water are formed as the byproduct(s). The mechanism is believed to involve the formation of a manganese(III) alkoxide complex which degrades into the aldehyde and a manganese(III) hydride species. The latter reacts with the alcohol to form hydrogen gas and thereby regenerates the alkoxide complex.
Original languageEnglish
JournalChemistry: A European Journal
Volume25
Issue number25
Pages (from-to)6439-6446
Number of pages8
ISSN0947-6539
DOIs
Publication statusPublished - 2019

Keywords

  • Alcohols
  • Dehydrogenation
  • Homogeneous catalysis
  • Manganese
  • Synthetic methods

Cite this

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title = "Manganese(III) Porphyrin-Catalyzed Dehydrogenation of Alcohols to form Imines, Tertiary Amines and Quinolines",
abstract = "Manganese(III) porphyrin chloride complexes have been developed for the first time as catalysts for the acceptorless dehydrogenative coupling of alcohols and amines. The reaction has been applied to the direct synthesis of imines, tertiary amines and quinolines where only hydrogen gas and/or water are formed as the byproduct(s). The mechanism is believed to involve the formation of a manganese(III) alkoxide complex which degrades into the aldehyde and a manganese(III) hydride species. The latter reacts with the alcohol to form hydrogen gas and thereby regenerates the alkoxide complex.",
keywords = "Alcohols, Dehydrogenation, Homogeneous catalysis, Manganese, Synthetic methods",
author = "Kobra Azizi and Sedigheh Akrami and Robert Madsen",
year = "2019",
doi = "10.1002/chem.201900737",
language = "English",
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pages = "6439--6446",
journal = "Chemistry: A European Journal",
issn = "0947-6539",
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}

Manganese(III) Porphyrin-Catalyzed Dehydrogenation of Alcohols to form Imines, Tertiary Amines and Quinolines. / Azizi, Kobra; Akrami, Sedigheh; Madsen, Robert.

In: Chemistry: A European Journal, Vol. 25, No. 25, 2019, p. 6439-6446.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Manganese(III) Porphyrin-Catalyzed Dehydrogenation of Alcohols to form Imines, Tertiary Amines and Quinolines

AU - Azizi, Kobra

AU - Akrami, Sedigheh

AU - Madsen, Robert

PY - 2019

Y1 - 2019

N2 - Manganese(III) porphyrin chloride complexes have been developed for the first time as catalysts for the acceptorless dehydrogenative coupling of alcohols and amines. The reaction has been applied to the direct synthesis of imines, tertiary amines and quinolines where only hydrogen gas and/or water are formed as the byproduct(s). The mechanism is believed to involve the formation of a manganese(III) alkoxide complex which degrades into the aldehyde and a manganese(III) hydride species. The latter reacts with the alcohol to form hydrogen gas and thereby regenerates the alkoxide complex.

AB - Manganese(III) porphyrin chloride complexes have been developed for the first time as catalysts for the acceptorless dehydrogenative coupling of alcohols and amines. The reaction has been applied to the direct synthesis of imines, tertiary amines and quinolines where only hydrogen gas and/or water are formed as the byproduct(s). The mechanism is believed to involve the formation of a manganese(III) alkoxide complex which degrades into the aldehyde and a manganese(III) hydride species. The latter reacts with the alcohol to form hydrogen gas and thereby regenerates the alkoxide complex.

KW - Alcohols

KW - Dehydrogenation

KW - Homogeneous catalysis

KW - Manganese

KW - Synthetic methods

U2 - 10.1002/chem.201900737

DO - 10.1002/chem.201900737

M3 - Journal article

VL - 25

SP - 6439

EP - 6446

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 0947-6539

IS - 25

ER -