Vanadium-and chromium-catalyzed dehydrogenative synthesis of imines from alcohols and amines

Yulong Miao; Simone Vestermann Samuelsen; Robert Madsen

doi:10.1021/acs.organomet.1c00123

Vanadium-and chromium-catalyzed dehydrogenative synthesis of imines from alcohols and amines

Yulong Miao, Simone Vestermann Samuelsen, Robert Madsen^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

Vanadium(IV) tetraphenylporphyrin dichloride and chromium(III) tetraphenylporphyrin chloride have been developed as catalysts for the acceptorless dehydrogenation of alcohols. The catalysts have been applied to the direct synthesis of imines in overall good yields from a variety of alcohols and amines. The transformations are proposed to proceed by metal−ligand bifunctional pathways with an outer-sphere transfer of two hydrogen atoms from the alcohol to the metal porphyrin complexes. The results show that vanadium and chromium catalysts can also be employed for the dehydrogenation of alcohols with the release of hydrogen gas, and they may represent valuable alternatives to other catalysts based on Earth-abundant metals.

Original language	English
Journal	Organometallics
Volume	40
Issue number	9
Pages (from-to)	1328-1335
ISSN	0276-7333
DOIs	https://doi.org/10.1021/acs.organomet.1c00123
Publication status	Published - 2021

Bibliographical note

Funding Information:
Y.M. and S.V.S. gratefully acknowledge the China Scholarship Council (CSC) and the Technical University of Denmark, respectively, for PhD fellowships. In addition, we thank the Independent Research Fund Denmark—Technology and Production Sciences for financial support.

Publisher Copyright:
© 2021 American Chemical Society

Access to Document

10.1021/acs.organomet.1c00123

OpenUrl availability

Full text

Cite this

@article{768fe2d4c6e4409ba4290cc4ff70c92f,

title = "Vanadium-and chromium-catalyzed dehydrogenative synthesis of imines from alcohols and amines",

abstract = "Vanadium(IV) tetraphenylporphyrin dichloride and chromium(III) tetraphenylporphyrin chloride have been developed as catalysts for the acceptorless dehydrogenation of alcohols. The catalysts have been applied to the direct synthesis of imines in overall good yields from a variety of alcohols and amines. The transformations are proposed to proceed by metal−ligand bifunctional pathways with an outer-sphere transfer of two hydrogen atoms from the alcohol to the metal porphyrin complexes. The results show that vanadium and chromium catalysts can also be employed for the dehydrogenation of alcohols with the release of hydrogen gas, and they may represent valuable alternatives to other catalysts based on Earth-abundant metals.",

author = "Yulong Miao and Samuelsen, {Simone Vestermann} and Robert Madsen",

note = "Funding Information: Y.M. and S.V.S. gratefully acknowledge the China Scholarship Council (CSC) and the Technical University of Denmark, respectively, for PhD fellowships. In addition, we thank the Independent Research Fund Denmark—Technology and Production Sciences for financial support. Publisher Copyright: {\textcopyright} 2021 American Chemical Society",

year = "2021",

doi = "10.1021/acs.organomet.1c00123",

language = "English",

volume = "40",

pages = "1328--1335",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Vanadium-and chromium-catalyzed dehydrogenative synthesis of imines from alcohols and amines

AU - Miao, Yulong

AU - Samuelsen, Simone Vestermann

AU - Madsen, Robert

N1 - Funding Information: Y.M. and S.V.S. gratefully acknowledge the China Scholarship Council (CSC) and the Technical University of Denmark, respectively, for PhD fellowships. In addition, we thank the Independent Research Fund Denmark—Technology and Production Sciences for financial support. Publisher Copyright: © 2021 American Chemical Society

PY - 2021

Y1 - 2021

N2 - Vanadium(IV) tetraphenylporphyrin dichloride and chromium(III) tetraphenylporphyrin chloride have been developed as catalysts for the acceptorless dehydrogenation of alcohols. The catalysts have been applied to the direct synthesis of imines in overall good yields from a variety of alcohols and amines. The transformations are proposed to proceed by metal−ligand bifunctional pathways with an outer-sphere transfer of two hydrogen atoms from the alcohol to the metal porphyrin complexes. The results show that vanadium and chromium catalysts can also be employed for the dehydrogenation of alcohols with the release of hydrogen gas, and they may represent valuable alternatives to other catalysts based on Earth-abundant metals.

AB - Vanadium(IV) tetraphenylporphyrin dichloride and chromium(III) tetraphenylporphyrin chloride have been developed as catalysts for the acceptorless dehydrogenation of alcohols. The catalysts have been applied to the direct synthesis of imines in overall good yields from a variety of alcohols and amines. The transformations are proposed to proceed by metal−ligand bifunctional pathways with an outer-sphere transfer of two hydrogen atoms from the alcohol to the metal porphyrin complexes. The results show that vanadium and chromium catalysts can also be employed for the dehydrogenation of alcohols with the release of hydrogen gas, and they may represent valuable alternatives to other catalysts based on Earth-abundant metals.

U2 - 10.1021/acs.organomet.1c00123

DO - 10.1021/acs.organomet.1c00123

M3 - Journal article

AN - SCOPUS:85106531449

SN - 0276-7333

VL - 40

SP - 1328

EP - 1335

JO - Organometallics

JF - Organometallics

IS - 9

ER -

Vanadium-and chromium-catalyzed dehydrogenative synthesis of imines from alcohols and amines

Abstract

Bibliographical note

Access to Document

OpenUrl availability

Fingerprint

Cite this