Molecular Diversity, Journal Year: 2024, Volume and Issue: unknown
Published: Nov. 25, 2024
Language: Английский
Chem Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 101295 - 101295
Published: March 1, 2025
Language: Английский
Citations
0
Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)
Published: April 19, 2025
Language: Английский
Citations
0
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 3, 2024
The high percentage of sp
Language: Английский
Citations
3
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(24), P. 18799 - 18809
Published: Dec. 11, 2024
Transition-metal-catalyzed cycloaddition reactions of strained small-ring compounds are powerful methods for constructing carbo- and heterocyclic structures medicinal interest. However, the application this strategy to bicyclo[1.1.0]butanes (BCBs), which among most carbocycles known, remains underdeveloped. Herein, we report vinylbicyclo[1.1.0]butane (VBCB) as a platform synthon palladium-catalyzed formal [2σ+2π] with various 2π-components, enabling synthesis BCHs, oxa-BCHs, aza-BCHs under identical reaction conditions. The zwitterionic π-allyl-Pd species generated through activation VBCBs is key circumventing potential carbene reactivity serves common intermediate cycloadditions diverse 2π-systems, including alkenes, aldehydes, ketones, imines. Notably, by utilizing Pd2(dba)3 an anthracene-derived Trost ligand, wide array BCHs bearing two vicinal chiral centers has been prepared in highly diastereo-, enantioselective manner. generality practicality method have demonstrated broad substrate scope, scale-up reactions, versatile transformation multiple functional groups into BCH scaffolds. Preliminary mechanistic studies support formation species.
Language: Английский
Citations
3
Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(40)
Published: May 31, 2024
Abstract Bridged cyclobutanes and sulfur heterocycles are currently under intense investigation as building blocks for pharmaceutical drug design. Two formal cycloaddition modes involving bicyclobutanes (BCBs) pyridinium 1,4‐zwitterionic thiolate derivatives were described to rapidly expand the chemical space of sulfur‐containing bridged cyclobutanes. By using Ni(ClO 4 ) 2 catalyst, an uncommon higher‐order (5+3) BCBs with quinolinium was achieved broad substrate scope mild reaction conditions. Furthermore, first Lewis acid‐catalyzed asymmetric polar BCB pyridazinium accomplished. In contrast, thiolates undergo Sc(OTf) 3 ‐catalyzed (3+3) generate thia‐norpinene products, which represent initial instance synthesizing 2‐thiabicyclo[3.1.1]heptanes (thia‐BCHeps) from BCBs. Moreover, we have successfully used this protocol prepare thia‐BCHeps‐substituted analogues bioactive molecule Pitofenone. Density functional theory (DFT) computations imply that kinetic factors govern between thiolate, whereas is thermodynamic control.
Language: Английский
Citations
2
Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110213 - 110213
Published: Aug. 1, 2024
Language: Английский
Citations
2
Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(25)
Published: April 11, 2024
Abstract While polyborylated alkenes are being recognized for their elevated status as highly valuable reagents in modern organic synthesis, allowing efficient access to a diverse array of transformations, including the formation C−C and C‐heteroatom bonds, potential energy‐transfer reactive groups has remained unexplored. Yet, this holds key generating elusive biradical species, which can be captured by olefins, thereby leading construction new highly‐borylated scaffolds. Herein, we report designed strategy photosensitized [2+2]‐cycloadditions poly‐borylated with various olefins enabling regioselective synthesis cyclobutane motifs, 1,1‐di‐, 1,1,2‐tri‐, 1,1,2,2‐tetra‐borylated cyclobutanes. In fact, these compounds belong family that presently lacks synthetic pathways. Interestingly, when α‐methylstyrene was used, reaction involves an interesting 1,5‐hydrogen atom transfer (HAT). Mechanistic deuterium‐labeling studies have provided insight into outcome process. addition, cyclobutanes then demonstrated useful selective oxidation processes resulting cyclobutanones γ‐lactones.
Language: Английский
Citations
1
Published: Aug. 16, 2024
Energy transfer catalysis (EnT) has had a profound impact on contemporary organic synthesis enabling the construction of higher in energy, complex molecules, via efficient access to triplet excited state. Despite this, intermolecular reactivity, and unique possibility several reaction pathways central diradical rendered control over outcomes, an intractable challenge. Extended chromophores such as non-symmetrical dienes have potential undergo 2+2 cycloaddition, 4+2 cycloaddition or geometric isomerization, which, combination with other mechanistic considerations (site- regioselectivity), results chemical reactions that are challenging regulate. Leveraging spin density predictive tool, use core functionality can be adequately tuned potentially modulate would highly revealing intimate links between structure EnT induced reactivity. Herein, we utilize boron tool explore reactivity under catalysis, paying particular attention hybridization effects target Through site- regioselective was realized employed motif effecting efficiency. Reaction divergence enable achieved, while counterintuitive regiodivergence observed isomerization versus cycloaddition. The validated in-depth investigation determining origin competing processes
Language: Английский
Citations
1
Chemical Communications, Journal Year: 2024, Volume and Issue: 60(62), P. 8075 - 8078
Published: Jan. 1, 2024
A mild Pd-catalyzed three-component cascade cyclization functionalization of
Language: Английский
Citations
0
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(15), P. 11490 - 11497
Published: July 18, 2024
Language: Английский
Citations
0