Co(III) or Ru(II)-Catalyzed Selective C–H Alkynylation of 2-Pyridones and Their Derivatives with Bromoalkynes DOI

Quanjian Luo,

Han‐Chi Wang,

Jierui Zhou

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 5, 2024

We successfully reported selective C–H alkynylation of 2-pyridones with bromoalkynes under the catalysis Co(III) or Ru(II). The reaction used easily accessible instead high-valent iodine alkynes. There is a broad substrate scope good yields. In addition, 2-pyridone can be as weakly directing group for proximal aryl bond. This method offers an efficient approach synthesizing diverse derivatives, yielding alkynylated products up to 95% yield (>40 examples).

Language: Английский

Weak‐Chelation Assisted Regioselective Indole C(4)‐Alkynylation via Six‐Membered Cobaltacycle Intermediate DOI

Sofaya Joshi,

Riya Dutta, Shyam Kumar Banjare

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1341 - 1347

Published: Jan. 13, 2024

Abstract Herein a regioselective indole C4‐alkynylation has been uncovered utilizing an earth‐abundant cobalt(III)‐catalyst. For this process, (bromoethynyl)benzene was used as alkynylating agent. Also, after screening various amide‐protected chelating groups we found dimethyl‐amide is optimal for the in‐situ generation of cobaltacycle intermediate. The six‐membered intermediate detected through high‐resolution mass spectrometry HRMS, which key conversion. Further, mechanistic studies were performed such KIE experiments, and reactions with radical scavengers, based on results plausible mechanism proposed. Moreover, to show application methodology, product oxidized diketone, monoketone, alkene, alkane further derivatized tricycle derivative, core structure many natural products.

Language: Английский

Citations

5
Uncovering the Reactivity of Cobalt‐Catalyst Towards Regioselective Hydroarylation of 1,6‐Diyne via Weak‐Chelation Assisted C−H Bond Activation DOI
Shyam Kumar Banjare,

Saista Afreen,

Pranav Shridhar Mahulkar

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(12), P. 1977 - 1982

Published: June 2, 2023

Abstract Herein, we report the reactivity of cobalt(III)‐catalyst towards hydroarylative functionalization 1,6‐diyne, which has never been explored before. The N ‐aryl lactam is prime substrate that undergoes sp 2 C−H bond activation. C−Co(III) formation occurs through weakly coordinating group. reaction mechanism reveals in‐situ a six‐membered cobaltacycle further with 1,6‐diyne. Also, radical quenching experiments suggest involvement ionic pathway for this conversion. In addition, hydrogen scrambling and kinetic isotope support proposed mechanism. A wide range electronically biased substrates reacting partners work well method in highly atom‐economical fashion.

Language: Английский

Citations

5
Co(III)-Catalyzed C6-Selective C–H Activation/Pyridine Migration of 2-Pyridones with Propiolates DOI

Yuelu Zhu,

Na Zhao,

Xin-Long Fu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: unknown

Published: Dec. 21, 2023

A versatile Co(III)-catalyzed C6-selective C–H activation/pyridine migration of 2-pyridones with available propiolates as coupling partners was demonstrated. This method features high atom economy, excellent regioselectivity, and good functional group tolerance by employing an inexpensive Co(III) catalyst under mild reaction conditions. Moreover, gram-scale synthesis late-stage modifications pharmaceuticals were performed to prove the effectiveness these synthetic approaches.

Language: Английский

Citations

3
Co(III) or Ru(II)-Catalyzed Selective C–H Alkynylation of 2-Pyridones and Their Derivatives with Bromoalkynes DOI

Quanjian Luo,

Han‐Chi Wang,

Jierui Zhou

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 5, 2024

We successfully reported selective C–H alkynylation of 2-pyridones with bromoalkynes under the catalysis Co(III) or Ru(II). The reaction used easily accessible instead high-valent iodine alkynes. There is a broad substrate scope good yields. In addition, 2-pyridone can be as weakly directing group for proximal aryl bond. This method offers an efficient approach synthesizing diverse derivatives, yielding alkynylated products up to 95% yield (>40 examples).

Language: Английский

Citations

0