Deconstructive diversification of cyclic amines

JB Roque, Y Kuroda, LT Göttemann, R Sarpong - Nature, 2018 - nature.com
Deconstructive functionalization involves carbon–carbon (C–C) bond cleavage followed by
bond construction on one or more of the constituent carbons. For example, ozonolysis and …

Deconstructive fluorination of cyclic amines by carbon-carbon cleavage

JB Roque, Y Kuroda, LT Göttemann, R Sarpong - Science, 2018 - science.org
Deconstructive functionalizations involving scission of carbon-carbon double bonds are well
established. In contrast, unstrained C (sp3)–C (sp3) bond cleavage and functionalization …

Deconstructive functionalizations of unstrained carbon–nitrogen cleavage enabled by difluorocarbene

J Su, X Ma, Z Ou, Q Song - ACS Central Science, 2020 - ACS Publications
Transition-metal-or oxidant-promoted deconstructive functionalizations of noncyclic carbon–
nitrogen bonds are well established, usually only leaving one moiety functionalized toward …

Ring-opening functionalizations of unstrained cyclic amines enabled by difluorocarbene transfer

Y Kim, J Heo, D Kim, S Chang, S Seo - Nature Communications, 2020 - nature.com
Chemical synthesis based on the skeletal variation has been prolifically utilized as an
attractive approach for modification of molecular properties. Given the ubiquity of unstrained …

Ring opening reactions of nitrogen heterocycles

AV Smolobochkin, AS Gazizov… - Russian Chemical …, 2019 - iopscience.iop.org
Published data on ring opening reactions of nitrogen-containing cyclic compounds resulting
in various acyclic products are integrated and systematized. The reactions of common five …

Biopatterned reorganization of alkaloids enabled by ring-opening functionalization of tertiary amines

H Lim, S Seong, Y Kim, S Seo… - Journal of the American …, 2021 - ACS Publications
Biosynthetic processes often involve reorganization of one family of natural products to
another. Chemical emulation of nature's rearrangement-based structural diversification …

Selective C–N Bond Cleavage in Unstrained Pyrrolidines Enabled by Lewis Acid and Photoredox Catalysis

K Aida, M Hirao, T Saitoh, T Yamamoto… - Journal of the …, 2024 - ACS Publications
Cleavage of inert C–N bonds in unstrained azacycles such as pyrrolidine remains a
formidable challenge in synthetic chemistry. To address this, we introduce an effective …

A Strategy for the Formal C− N Cross‐Coupling of Tertiary Amines

PR Ledwith, ML Cooney, KA Bahou… - Angewandte …, 2024 - Wiley Online Library
We report a strategy for the formal C− N cross‐coupling of tertiary amines via the in situ
generation and displacement of N‐acyl ammonium species. Specifically, treatment of …

Key Mechanistic Features of the Silver (I)-Mediated Deconstructive Fluorination of Cyclic Amines: Multistate Reactivity versus Single-Electron Transfer

JB Roque, R Sarpong, DG Musaev - Journal of the American …, 2021 - ACS Publications
Density functional calculations have provided evidence that a Ag (I)-mediated
deconstructive fluorination of N-benzoylated cyclic amines (LH) with Selectfluor [(F …

Selective Cleavage and Tunable Functionalization of the C–C/C–N Bonds of N-Arylpiperidines Promoted by tBuONO

Y He, Z Zheng, Y Liu, J Qiao, X Zhang, X Fan - Organic letters, 2019 - ACS Publications
In this paper, selective cleavage and tunable functionalization of the inert C–C/C–N bonds in
N-arylpiperidines promoted by t BuONO under metal-free conditions is presented. To be …