Visible Light-Induced C–H Alkylation of Azauracils with N-Hydroxyphthalimide Esters via Catalytic EDA Complex

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 13, 2025

Herein, we report sodium iodide (NaI)-catalyzed decarboxylative C–H alkylation of azauracils with N-hydroxyphthalimide (NHPI) esters facilitated by visible light activation catalytic electron donor–acceptor (EDA) complexes. Control experiments and density functional theory calculations suggest that the coupling reaction proceeds via a transiently assembled EDA complex between NHPI ester NaI in N,N-dimethylacetamide solvent. This synthetic method efficiently applies to primary, secondary, tertiary under mild, photocatalyst-free, redox-neutral conditions, achieving high yields desired alkylated azauracils.

Language: Английский

---

Visible-light-driven EDA complex-promoted cascade cyclization to construct 4-cyanoalkyl isoquinoline-1,3-diones

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(21), P. 2958 - 2961

Published: Jan. 1, 2024

Visible-light-driven EDA complex-promoted ring-opening of cycloketone oxime esters to synthesise various 4-cyanoalkylated isoquinoline-1,3-diones with acryloylbenzamides was developed.

Language: Английский

---

Visible-light-induced decarboxylative cascade cyclization of acryloylbenzamides with N-hydroxyphthalimide esters via EDA complexes

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(5), P. 965 - 969

Published: Jan. 1, 2024

A visible-light-induced, electron donor–acceptor (EDA) complex-enabled decarboxylative cascade reaction of acryloylbenzamides with alkyl N -hydroxyphthalimide esters by NaI/PPh 3 catalysis was developed.

Language: Английский

---

Visible light mediated photocatalytic aerobic oxidative synthesis of pyrazolo[4,3-d]pyrimidin-7(6H)-ones and sildenafil

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

Published: Jan. 1, 2025

A novel, efficient and sustainable visible-light–mediated methodology for the construction of pyrazolo[4,3- d ]pyrimidin-7(6 H )-ones from easily available starting materials has been developed.

Language: Английский

---

Visible-Light-Driven Tandem Cyclization of o-Hydroxyaryl Enaminones: Access to 3-(α-Arylsulfonamido)trifluoroethyl Chromones

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

A visible-light-driven intermolecular tandem α-amidotrifluoroethylation/cyclization of enaminones using a previously unreported N-trifluoroethylaminopyridinium salt was achieved in the absence transition metal catalysts or bases. Notable features this synthetic method include mild conditions, high selectivity, excellent functional group compatibility, and satisfactory yields. Preliminary mechanistic studies indicate that reaction proceeds via radical pathway, involving an situ generated N-trifluoroethyl radical, followed by 1,2-H shift.

Language: Английский

---

Electrochemical-induced solvent-tuned selective C(sp³)–H bond activation towards the synthesis of C3-functionalized chromone derivatives

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(38), P. 5050 - 5053

Published: Jan. 1, 2024

An unprecedented solvent-tuned electrochemical method for selective C(sp

Language: Английский

---