Dearomatizing radical cyclizations and cyclization cascades triggered by electron-transfer reduction of amide-type carbonyls

HM Huang, DJ Procter - Journal of the American Chemical …, 2017 - ACS Publications
Highly selective dearomatizing radical cyclizations and cyclization cascades, triggered by
single electron transfer to amide-type carbonyls by SmI2–H2O–LiBr, provide efficient access …

Diastereoselective Radical 1,4-Ester Migration: Radical Cyclizations of Acyclic Esters with SmI2

C Morrill, Á Péter, I Amalina, E Pye… - Journal of the …, 2022 - ACS Publications
Reductive cyclizations of carbonyl compounds, mediated by samarium (II) diiodide (SmI2,
Kagan's reagent), represent an invaluable platform to generate molecular complexity in a …

Biocatalytic Conversion of Cyclic Ketones Bearing α‐Quaternary Stereocenters into Lactones in an Enantioselective Radical Approach to Medium‐Sized Carbocycles

C Morrill, C Jensen, X Just‐Baringo… - Angewandte …, 2018 - Wiley Online Library
Cyclic ketones bearing α‐quaternary stereocenters underwent efficient kinetic resolution
using cyclohexanone monooxygenase (CHMO) from Acinetobacter calcoaceticus. Lactones …

Radical heterocyclization and heterocyclization cascades triggered by electron transfer to amide‐type carbonyl compounds

HM Huang, DJ Procter - Angewandte Chemie International …, 2017 - Wiley Online Library
Radical heterocyclizations triggered by electron transfer to amide‐type carbonyls, using
SmI2‐H2O, provide straightforward access to bicyclic heterocyclic scaffolds containing …

Mechanistic Study of SmI2/H2O and SmI2/Amine/H2O-Promoted Chemoselective Reduction of Aromatic Amides (Primary, Secondary, Tertiary) to Alcohols via …

SR Huq, S Shi, R Diao, M Szostak - The Journal of Organic …, 2017 - ACS Publications
Samarium (II) iodide–water and samarium (II) iodide–water–amine complexes have been
recognized as valuable reagents for the selective generation of aminoketyl radicals from …

Reductive cyclisations of amidines involving aminal radicals

HM Huang, RW Adams, DJ Procter - Chemical Communications, 2018 - pubs.rsc.org
Amidines bearing simple alkenes undergo aminal radical cyclisation upon treatment with
SmI2. The mild, reductive electron transfer process delivers medicinally-relevant, polycyclic …

Secondary amides as hydrogen atom transfer promoters for reactions of samarium diiodide

TV Chciuk, AM Li, A Vazquez-Lopez… - Organic …, 2017 - ACS Publications
Two secondary amides (N-methylacetamide and 2-pyrrolidinone) were used as additives
with SmI2 in THF to estimate the extent of N–H bond weakening upon coordination …

Reversibility of Ketone Reduction by SmI2–Water and Formation of Organosamarium Intermediates

TV Chciuk, WR Anderson Jr, RA Flowers - Organometallics, 2017 - ACS Publications
The reduction of ketones by SmI2–water has long been thought to proceed through a
reversible initial electron transfer with the formation of organosamarium intermediates in a …

A green strategy for the synthesis of sulfone derivatives of p-methylaminophenol: Kinetic evaluation and antibacterial susceptibility

D Nematollahi, S Khazalpour, M Ranjbar, S Momeni - Scientific reports, 2017 - nature.com
This is one of the few examples in which the diverse products have been synthesized just by
changing the applied potential. The synthesis of sulfonyl derivatives of p …

Selective construction of quaternary stereocentres in radical cyclisation cascades triggered by electron-transfer reduction of amide-type carbonyls

HM Huang, P Bonilla, DJ Procter - Organic & Biomolecular Chemistry, 2017 - pubs.rsc.org
Radical–radical cyclisation cascades, triggered by single-electron-transfer to amide-type
carbonyls using SmI2–H2O–LiBr, result in the selective construction of quaternary carbon …