Visible-light organophotoredox-mediated intermolecular formal [4 + 2] cycloadditions of arylcyclobutylamines with olefins

Luo, Zhengshan; Xing, Zequn; Gao, Rui; Han, Yifei; Ren, Jing; Wang, Zhongwen

doi:10.1039/d3ob00527e

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob00527e

|View full text |Cite

Visible-light organophotoredox-mediated intermolecular formal [4 + 2] cycloadditions of arylcyclobutylamines with olefins

Zhengshan Luo

Zequn Xing

Rui Gao

et al.

Abstract: We developed a visible-light organophotoredox-mediated formal [4+2] cycloaddition of arylcyclobutylamines with olefins, using QXPT-NPhCN as an organic photocatalyst. We found that addition of K3PO4 could significantly promote the cycloadditions. With...

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article3

Relationship

Self Cite0

Independent3

Authors

Journals

Cited by 3 publications

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Photoactivated Formal [3 + 2]/[4+2] Cycloaddition of N‐Aryl Cyclopropyl and Cyclobutylamines

Villela,

Zidan,

Barriault

2024

Eur J Org Chem

View full text Add to dashboard Cite

Organic transformations initiated by photochemical activation have been at the forefront of reaction discovery. In this study, we present a formal photochemical [3 + 2] and [4 + 2] cycloaddition using N‐aryl cyclopropylamines and N‐aryl cyclobutylamines in conjunction with α,β‐unsaturated carbonyl systems, unveiling two distinct mechanistic pathways. The [3 + 2] cycloaddition is elucidated as being guided by the photochemical activity of an electron donor‐acceptor (EDA) complex. Simultaneously, intermolecular [4 + 2] annulation of cyclobutylanilines is achieved by visible‐light photoredox catalysis. These simple methodologies have wide applicability, facilitating the synthesis of N‐arylaminocycloalkyl compounds in yields ranging from good to excellent

show abstract

Photoactivated Formal [3 + 2]/[4+2] Cycloaddition of N‐Aryl Cyclopropyl and Cyclobutylamines

Villela,

Zidan,

Barriault

2024

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

Exploring the Reactivity of Rigid 1-Azadienes Derived from Methylene γ-Lactams. Applications to the Stereoselective Synthesis of Spiro-γ-Lactams

López-Francés,

Serna-Burgos,

del Corte

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

Visible-light-enabled stereoselective synthesis of functionalized cyclohexylamine derivatives via [4 + 2] cycloadditions

Lu,

Che,

Zhen

et al. 2024

Chem. Sci.

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Visible-light organophotoredox-mediated intermolecular formal [4 + 2] cycloadditions of arylcyclobutylamines with olefins

Abstract: We developed a visible-light organophotoredox-mediated formal [4+2] cycloaddition of arylcyclobutylamines with olefins, using QXPT-NPhCN as an organic photocatalyst. We found that addition of K3PO4 could significantly promote the cycloadditions. With...

Cited by 3 publications

References 41 publications

Photoactivated Formal [3 + 2]/[4+2] Cycloaddition of N‐Aryl Cyclopropyl and Cyclobutylamines

Photoactivated Formal [3 + 2]/[4+2] Cycloaddition of N‐Aryl Cyclopropyl and Cyclobutylamines

Exploring the Reactivity of Rigid 1-Azadienes Derived from Methylene γ-Lactams. Applications to the Stereoselective Synthesis of Spiro-γ-Lactams

Visible-light-enabled stereoselective synthesis of functionalized cyclohexylamine derivatives via [4 + 2] cycloadditions

Contact Info

Product

Resources

About