Regioselective α-Phosphonylation of Unprotected Alicyclic AminesClick to copy article linkArticle link copied!
- Bowen LiBowen LiCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United StatesMore by Bowen Li
- Fuchao YuFuchao YuCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United StatesMore by Fuchao Yu
- Weijie ChenWeijie ChenCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United StatesMore by Weijie Chen
- Daniel Seidel*Daniel Seidel*Email: [email protected]Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United StatesMore by Daniel Seidel
Abstract
Unprotected alicyclic amines undergo α-C–H bond phosphonylation via a two-stage one-pot process involving the oxidation of amine-derived lithium amides with simple ketone oxidants, generating transient imines which are then captured with phosphites or phosphine oxides. Amines with an existing α-substituent undergo regioselective α′-phosphonylation. Amine α-arylation and α′-phosphonylation can be combined, generating a difunctionalized product in a single operation.
Cited By
Smart citations by scite.ai include citation statements extracted from the full text of the citing article. The number of the statements may be higher than the number of citations provided by ACS Publications if one paper cites another multiple times or lower if scite has not yet processed some of the citing articles.
This article is cited by 4 publications.
- Kamal Bhatt, Daniel Seidel. Cyclic Imine-BF3 Complexes as Precursors for Functionalized Azacycles. Synlett 2025, 36
(11)
, 1435-1440. https://doi.org/10.1055/a-2538-2165
- Jie Liu, Xiaolan Li, Guisheng Chen, Haiqing Luo. Silver‐Catalyzed Oxidative Ring‐Opening of Cyclic Aliphatic Amines for C−H Alkylation of Cyclic Aldimines. Advanced Synthesis & Catalysis 2025, 367
(11)
https://doi.org/10.1002/adsc.202500002
- Tiantian Zhang, Hexiang Wang, Liliang Huang, Junhai Huang, Huangdi Feng. A Cu/Cd-cocatalysed cascade reaction for constructing nitrogen-tethered 1,6-enynes enabled by 1,5-hydride transfer. Organic Chemistry Frontiers 2025, 23 https://doi.org/10.1039/D5QO00174A
- Timothy K. Beng, Ifeyinwa S. Anosike, Jasleen Kaur. Stereocontrolled and time-honored access to piperidine- and pyrrolidine-fused 3-methylenetetrahydropyrans using lactam-tethered alkenols. RSC Advances 2024, 14
(37)
, 26913-26919. https://doi.org/10.1039/D4RA04916K
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.