Expanding the Clip-and-Cleave Concept: Approaching Enantioselective C–H Hydroxylations by Copper Imine Complexes Using O2 and H2O2 as Oxidants DOI

Alexander Petrillo,

Kevin F. Kirchgeßner-Prado,

David A. Hiller

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(37), P. 25689 - 25700

Published: Sept. 6, 2024

Copper-mediated aromatic and aliphatic C-H hydroxylations using benign oxidants (O

Language: Английский

Strain-promoted azide-alkyne cycloaddition enhanced by the secondary interactions† DOI

Riko Yoshikawa,

Shohei Hamada, Jun‐ichi Matsuo

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Azide-alkyne cycloaddition of cyclooct-2-yn-1-ol and 2-(azidophenyl)boronic acid proceeded rapidly at room temperature with complete regioselectivity to afford a triazole having boronate ester group. The secondary interaction form ion contributed rate acceleration the control regioselectivity. an imine or hemiaminal was also evaluated.

Language: Английский

Citations

1
o-Halogenation and -Alkoxylation of Phenylglycine Derivatives by Pd-Mediated C-H Functionalization: Scope and Limitations DOI Creative Commons
Eduardo Laga, Sonia Nieto,

Carlos Cativiela

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(2), P. 236 - 236

Published: Jan. 9, 2025

Orthopalladated derivatives from substituted phenylglycines [Pd(μ-Cl)(C6H3R1C(R2)(R3)N(R4)2]2 (1) react with halogenating reagents (PhICl2, Br2, I2) (2) to give the corresponding o-halogenated amino acids C6H3(X)R1C(R2)(R3)N(R4)2 (3). The reaction is general and tolerates a variety of functional groups (R1 R4) at aryl ring, Cα, N atom. On other hand, PhI(OAc)2 in presence alcohols R5OH (4) gives o-alkoxylated C6H3(OR5)R1C(R2)(R3)N(R4)2 (5), also as process. A partial loss enantiomeric excess observed when starting phenylglycine enantiomerically pure, this arising formation bridging azavinylidene (6) imine intermediate species (7), which were characterized by X-ray diffraction methods.

Language: Английский

Citations

0
Copper-catalyzed aryl ortho-C–H thiolation of aldehydes via a transient directing group strategy DOI Creative Commons

Ming-Shun Mei,

Dong Kee Yi, Fanyi Meng

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

The Cu-catalyzed C–H thiolation reaction of aromatic aldehydes has been developed via a transient directing group strategy.

Language: Английский

Citations

0
Expanding the Clip-and-Cleave Concept: Approaching Enantioselective C–H Hydroxylations by Copper Imine Complexes Using O2 and H2O2 as Oxidants DOI

Alexander Petrillo,

Kevin F. Kirchgeßner-Prado,

David A. Hiller

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(37), P. 25689 - 25700

Published: Sept. 6, 2024

Copper-mediated aromatic and aliphatic C-H hydroxylations using benign oxidants (O

Language: Английский

Citations

2