A Pd-catalyzed formal [4 + 1] cycloaddition reaction of sulfur ylides and in situ-generated Pd-stabilized zwitterions offers a convenient route to a series of functionalized proline derivatives. The utility of this method is demonstrated by a gram-scale synthesis and chemoselective functionalization of a proline-based derivative.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10845110PMC
http://dx.doi.org/10.1021/acs.joc.3c02178DOI Listing

Publication Analysis

Top Keywords

pd-catalyzed annulation
4
annulation strategy
4
strategy functionalized
4
functionalized 4-methyleneproline
4
4-methyleneproline derivatives
4
derivatives pd-catalyzed
4
pd-catalyzed formal
4
formal cycloaddition
4
cycloaddition reaction
4
reaction sulfur
4

Similar Publications

A synthetic strategy of a palladium-catalyzed cascade annulation reaction followed by aerial oxidation was designed to construct 6-benzo[c]chromene scaffolds. Various 6-benzo[c]chromenes were synthesized under mild reaction conditions using easily accessible -QMs and commercially available -hydroxyarylboronic acids. One of the synthesized chromenes has been ambiguously confirmed by single-crystal XRD analysis.

View Article and Find Full Text PDF

Intermediate Control: Unlocking Hitherto Unknown Reactivity and Selectivity in N-Conjugated Allenes and Alkynes.

Acc Chem Res

January 2025

Department of Chemistry and Chemistry Institution for Functional Materials, Pusan National University, Busan 46241, Republic of Korea.

ConspectusControlling selectivity through manipulation of reaction intermediates remains one of the most enduring challenges in organic chemistry, providing novel solutions for selective C-C π-bond functionalization. This approach, guided by activation principles, provides an effective method for selective functional group installation, enabling direct synthesis of organic molecules that are inaccessible through conventional pathways. In particular, the selective functionalization of N-conjugated allenes and alkynes has emerged as a promising research focus, driven by advances in controlling reactive intermediates and activation strategies.

View Article and Find Full Text PDF

Ferrocenyl amines as directing groups for C-H activation have limitations as they are prone to undergo oxidation, allylic deamination, and β-hydride elimination. The fundamental challenge observed here is the competition between the desired C-H activation the vulnerable β-C-H bond activation of amines and fine-tuning of a suitable oxidant which avoids the oxidation of the β-C-H bond and ferrocene. Herein, the potential of an axially chiral NOBINAc ligand is revealed to implement the enantioselective Pd-catalyzed C-H activation process of ferrocenyl amines.

View Article and Find Full Text PDF

Two novel Pd-catalyzed protocols for the controllable synthesis of benzo[]furo[2,3-]azepines and furo[3,2-]indoles have been developed by intermolecular oxidative annulation of 2-(furan-2-yl)anilines and propargyl carbonates versus intramolecular C-H amination reactions. These two protocols feature great scalability, functional group tolerance, and relatively mild reaction conditions. Notably, the robust methodologies could also provide valuable opportunities for assembling azepine-fused benzothiophene, indole-fused benzothiophene, and indole-fused benzimidazole, which may have potential applications in the synthesis of related pharmaceuticals or polymeric materials.

View Article and Find Full Text PDF

Annulations through dual C-H activation represent a powerful tool to selectively assemble multi-cyclic scaffolds. We present herein a palladium-catalyzed -/-C-H-annulation of biphenyl amines with 1,6-enynes. This regioselective non-rollover cyclometallation was achieved through meticulous tuning of electronic factors of both the partners.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!