---
_id: '61335'
abstract:
- lang: eng
text: Amidines are a ubiquitous class of bioactive compounds found in a
wide variety of natural products; thus, efficient strategies for their preparation
are in great demand. Herein, a novel protocol is reported for the synthesis of
amidines based on PIII/PVO redox catalysis.
This two‐step, one‐pot approach involves the activation of amides via PIII/PVO
catalyzed in situ formation of imidoyl chloride intermediates which are directly
converted upon reaction with amines into the corresponding amidines. Instead of
traditionally used toxic and corrosive chloride sources, hexachloroacetone (HCA)
is successfully employed as a halide source. The reaction proceeds with low catalyst
loading (2 mol%) in BuOAc as the solvent. Under the optimized conditions, 20 amidines
are prepared in yields up to 99%. A feasible mechanism is proposed based on experimental
results. The synthetic potential of this method is evaluated in the preparation
of the tyrosine kinase inhibitor (TKI) Erlotinib.
article_number: '202500394'
author:
- first_name: Viktorija
full_name: Medvaric, Viktorija
id: '92677'
last_name: Medvaric
- first_name: Jan
full_name: Paradies, Jan
id: '53339'
last_name: Paradies
orcid: 0000-0002-3698-668X
- first_name: Thomas
full_name: Werner, Thomas
id: '89271'
last_name: Werner
orcid: 0000-0001-9025-3244
citation:
ama: Medvaric V, Paradies J, Werner T. Synthesis of Amidines Via P(III)/P(V)=O Redox
Catalyzed In Situ Formation of Imidoyl Chlorides From Amides. Advanced Synthesis
and Catalysis. Published online 2025. doi:10.1002/adsc.70059
apa: Medvaric, V., Paradies, J., & Werner, T. (2025). Synthesis of Amidines
Via P(III)/P(V)=O Redox Catalyzed In Situ Formation of Imidoyl Chlorides From
Amides. Advanced Synthesis and Catalysis, Article 202500394. https://doi.org/10.1002/adsc.70059
bibtex: '@article{Medvaric_Paradies_Werner_2025, title={Synthesis of Amidines Via
P(III)/P(V)=O Redox Catalyzed In Situ Formation of Imidoyl Chlorides From Amides},
DOI={10.1002/adsc.70059}, number={202500394},
journal={Advanced Synthesis and Catalysis}, publisher={Wiley}, author={Medvaric,
Viktorija and Paradies, Jan and Werner, Thomas}, year={2025} }'
chicago: Medvaric, Viktorija, Jan Paradies, and Thomas Werner. “Synthesis of Amidines
Via P(III)/P(V)=O Redox Catalyzed In Situ Formation of Imidoyl Chlorides From
Amides.” Advanced Synthesis and Catalysis, 2025. https://doi.org/10.1002/adsc.70059.
ieee: 'V. Medvaric, J. Paradies, and T. Werner, “Synthesis of Amidines Via P(III)/P(V)=O
Redox Catalyzed In Situ Formation of Imidoyl Chlorides From Amides,” Advanced
Synthesis and Catalysis, Art. no. 202500394, 2025, doi: 10.1002/adsc.70059.'
mla: Medvaric, Viktorija, et al. “Synthesis of Amidines Via P(III)/P(V)=O Redox
Catalyzed In Situ Formation of Imidoyl Chlorides From Amides.” Advanced Synthesis
and Catalysis, 202500394, Wiley, 2025, doi:10.1002/adsc.70059.
short: V. Medvaric, J. Paradies, T. Werner, Advanced Synthesis and Catalysis (2025).
date_created: 2025-09-17T15:16:49Z
date_updated: 2025-11-10T08:44:04Z
department:
- _id: '2'
- _id: '389'
doi: 10.1002/adsc.70059
keyword:
- T2
- T
- CSSD
language:
- iso: eng
publication: Advanced Synthesis and Catalysis
publication_identifier:
issn:
- 1615-4150
- 1615-4169
publication_status: published
publisher: Wiley
status: public
title: Synthesis of Amidines Via P(III)/P(V)=O Redox Catalyzed In Situ Formation of
Imidoyl Chlorides From Amides
type: journal_article
user_id: '89271'
year: '2025'
...
---
_id: '61336'
article_number: jacs.5c06190
author:
- first_name: Rundong
full_name: Zhou, Rundong
last_name: Zhou
- first_name: Viktorija
full_name: Medvaric, Viktorija
id: '92677'
last_name: Medvaric
- first_name: Thomas
full_name: Werner, Thomas
id: '89271'
last_name: Werner
orcid: https://orcid.org/0000-0001-9025-3244
- first_name: Jan
full_name: Paradies, Jan
id: '53339'
last_name: Paradies
orcid: 0000-0002-3698-668X
citation:
ama: 'Zhou R, Medvaric V, Werner T, Paradies J. Metal-Free Reduction of Nitrous
Oxide via PIII/PV═O Cycling: Mechanistic Insights and Catalytic
Performance. Journal of the American Chemical Society. Published online
2025. doi:10.1021/jacs.5c06190'
apa: 'Zhou, R., Medvaric, V., Werner, T., & Paradies, J. (2025). Metal-Free
Reduction of Nitrous Oxide via PIII/PV═O Cycling: Mechanistic
Insights and Catalytic Performance. Journal of the American Chemical Society,
Article jacs. 5c06190. https://doi.org/10.1021/jacs.5c06190'
bibtex: '@article{Zhou_Medvaric_Werner_Paradies_2025, title={Metal-Free Reduction
of Nitrous Oxide via PIII/PV═O Cycling: Mechanistic Insights
and Catalytic Performance}, DOI={10.1021/jacs.5c06190},
number={jacs. 5c06190}, journal={Journal of the American Chemical Society}, publisher={American
Chemical Society (ACS)}, author={Zhou, Rundong and Medvaric, Viktorija and Werner,
Thomas and Paradies, Jan}, year={2025} }'
chicago: 'Zhou, Rundong, Viktorija Medvaric, Thomas Werner, and Jan Paradies. “Metal-Free
Reduction of Nitrous Oxide via PIII/PV═O Cycling: Mechanistic
Insights and Catalytic Performance.” Journal of the American Chemical Society,
2025. https://doi.org/10.1021/jacs.5c06190.'
ieee: 'R. Zhou, V. Medvaric, T. Werner, and J. Paradies, “Metal-Free Reduction of
Nitrous Oxide via PIII/PV═O Cycling: Mechanistic Insights
and Catalytic Performance,” Journal of the American Chemical Society, Art.
no. jacs. 5c06190, 2025, doi: 10.1021/jacs.5c06190.'
mla: 'Zhou, Rundong, et al. “Metal-Free Reduction of Nitrous Oxide via PIII/PV═O
Cycling: Mechanistic Insights and Catalytic Performance.” Journal of the American
Chemical Society, jacs. 5c06190, American Chemical Society (ACS), 2025, doi:10.1021/jacs.5c06190.'
short: R. Zhou, V. Medvaric, T. Werner, J. Paradies, Journal of the American Chemical
Society (2025).
date_created: 2025-09-17T15:18:11Z
date_updated: 2025-11-10T08:43:50Z
department:
- _id: '2'
- _id: '389'
doi: 10.1021/jacs.5c06190
keyword:
- T2
- CSSD
language:
- iso: eng
publication: Journal of the American Chemical Society
publication_identifier:
issn:
- 0002-7863
- 1520-5126
publication_status: published
publisher: American Chemical Society (ACS)
status: public
title: 'Metal-Free Reduction of Nitrous Oxide via PIII/PV═O
Cycling: Mechanistic Insights and Catalytic Performance'
type: journal_article
user_id: '89271'
year: '2025'
...