Organocatalytic α-Aminoalkylation of Azomethine Imines by α-Silylamines under Blue LED Light

Jiacheng Li; Lorenzo Carli; Sara Helen Kyne; Philip Wai Hong Chan

doi:10.1002/adsc.202300463

Organocatalytic α-Aminoalkylation of Azomethine Imines by α-Silylamines under Blue LED Light

Jiacheng Li
, Lorenzo Carli
, Sara Helen Kyne
, Philip Wai Hong Chan

School of Chemistry

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

12 Citations (Scopus)

Abstract

A synthetic method to prepare 1,2-diamines efficiently that relies on the 4CzPN-catalysed α-aminoalkylation of azomethine imines by secondary and tertiary α-silylamines under blue light emitting diode (LED) light (456 nm) is described. Achieved under metal- and additive-free reaction conditions at room temperature, the synthetic protocol was shown to afford product yields up to 99% and applicable to the late-stage functionalisation of three drug molecules and the gramme-scale preparation of one example.

Original language	English
Pages (from-to)	2422-2427
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	365
Issue number	14
DOIs	https://doi.org/10.1002/adsc.202300463
Publication status	Published - 18 Jul 2023

Keywords

1,2-diamines
azomethine imines
photoredox catalysis
α-aminoalkylation
α-silylamines

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10.1002/adsc.202300463Licence: CC BY-NC-ND

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title = "Organocatalytic α-Aminoalkylation of Azomethine Imines by α-Silylamines under Blue LED Light",

abstract = "A synthetic method to prepare 1,2-diamines efficiently that relies on the 4CzPN-catalysed α-aminoalkylation of azomethine imines by secondary and tertiary α-silylamines under blue light emitting diode (LED) light (456 nm) is described. Achieved under metal- and additive-free reaction conditions at room temperature, the synthetic protocol was shown to afford product yields up to 99\% and applicable to the late-stage functionalisation of three drug molecules and the gramme-scale preparation of one example.",

keywords = "1,2-diamines, azomethine imines, photoredox catalysis, α-aminoalkylation, α-silylamines",

author = "Jiacheng Li and Lorenzo Carli and Kyne, \{Sara Helen\} and Chan, \{Philip Wai Hong\}",

note = "Funding Information: This work was supported by a Discovery Project Grant (DP210103425) from the Australian Research Council. Open access publishing facilitated by Monash University, as part of the Wiley ‐ Monash University agreement via the Council of Australian University Librarians. Publisher Copyright: {\textcopyright} 2023 The Authors. Advanced Synthesis \& Catalysis published by Wiley-VCH GmbH.",

year = "2023",

month = jul,

day = "18",

doi = "10.1002/adsc.202300463",

language = "English",

volume = "365",

pages = "2422--2427",

journal = "Advanced Synthesis and Catalysis",

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AU - Li, Jiacheng

AU - Carli, Lorenzo

AU - Kyne, Sara Helen

AU - Chan, Philip Wai Hong

N1 - Funding Information: This work was supported by a Discovery Project Grant (DP210103425) from the Australian Research Council. Open access publishing facilitated by Monash University, as part of the Wiley ‐ Monash University agreement via the Council of Australian University Librarians. Publisher Copyright: © 2023 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH.

PY - 2023/7/18

Y1 - 2023/7/18

N2 - A synthetic method to prepare 1,2-diamines efficiently that relies on the 4CzPN-catalysed α-aminoalkylation of azomethine imines by secondary and tertiary α-silylamines under blue light emitting diode (LED) light (456 nm) is described. Achieved under metal- and additive-free reaction conditions at room temperature, the synthetic protocol was shown to afford product yields up to 99% and applicable to the late-stage functionalisation of three drug molecules and the gramme-scale preparation of one example.

AB - A synthetic method to prepare 1,2-diamines efficiently that relies on the 4CzPN-catalysed α-aminoalkylation of azomethine imines by secondary and tertiary α-silylamines under blue light emitting diode (LED) light (456 nm) is described. Achieved under metal- and additive-free reaction conditions at room temperature, the synthetic protocol was shown to afford product yields up to 99% and applicable to the late-stage functionalisation of three drug molecules and the gramme-scale preparation of one example.

KW - 1,2-diamines

KW - azomethine imines

KW - photoredox catalysis

KW - α-aminoalkylation

KW - α-silylamines

UR - https://www.scopus.com/pages/publications/85164512743

U2 - 10.1002/adsc.202300463

DO - 10.1002/adsc.202300463

M3 - Article

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VL - 365

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JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 14

ER -

Organocatalytic α-Aminoalkylation of Azomethine Imines by α-Silylamines under Blue LED Light

Abstract

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New catalytic alkyne cyclisation strategies for complex molecule synthesis

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Organocatalytic α-Aminoalkylation of Azomethine Imines by α-Silylamines under Blue LED Light

Abstract

Keywords

Access to Document

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New catalytic alkyne cyclisation strategies for complex molecule synthesis

Cite this