Selective Oxidative Methyl C–H Functionalization of Butylated Hydroxytoluene toward Arylimines/N-Heterocycles DOI
Jianyu Dong,

Shaofeng Wu,

Furong Geng

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(20), P. 14649 - 14658

Published: Oct. 10, 2023

A metal-free and selective oxidative methyl C-H functionalization of BHT with aniline compounds has been developed. This innovative method enables the facile efficient synthesis a diverse array BHT-functionalized N-containing skeletons, including arylamines, benzoxazoles, benzothiazoles, benzimidazoles, quinazolines, quinazolinones, all which are challenging to access. The control experiment involving TEMP18O suggests that radical adduct TEMPO benzyl may serve as an intermediate.

Language: Английский

Cascade Cyclization/Amination of para‐Quinone Methides with β‐Ketodinitriles: Synthesis of Polysubstituted Furans DOI

Liyong Fan,

Longzhi Zhu,

Wenli Shang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(9), P. 2101 - 2108

Published: March 5, 2024

Abstract A protocol for the synthesis of trisubstituted furans via phosphoric acid‐catalyzed regioselective cascade cyclization/amination para ‐quinone methides ( p ‐QMs) with β ‐ketodinitriles has been disclosed first time. Various kinds ‐QMs and can effectively produce desired polysubstituted furan derivatives in 64–95% yields, demonstrating high atomic economy their application construction heterocycles. Preliminary biological activity assay suggests that these have potential anticancer activities.

Language: Английский

Citations

3
Copper‐Catalyzed Regioselective Cyanation/Diarylmethylation of Formamides: Construction of α‐Cyano Functionalized Tetra‐Substituted Olefins DOI

Minjing Yuan,

Zikang Li, Weifeng Xu

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 14, 2024

Comprehensive Summary A copper‐catalyzed cyanation/diarylmethylation of formamides has been developed for the synthesis α‐cyano functionalized tetra‐substituted olefins by utilizing para ‐quinone methides ( p ‐QMs) and trimethylcyanosilane as functionalization sources. Various kinds ‐QMs are well tolerated, delivering desired products with 72%—94% yields, demonstrating broad functional group tolerance. Notably, reaction does not require noble metals proceeds regioselectively under mild conditions. Based on step‐by‐step control experiments, Hammett studies DFT calculation, a plausible mechanism is proposed.

Language: Английский

Citations

0
Iron-Catalyzed Cross-Dehydrogenative Coupling of para-Quinone Methides with Formamides: In Situ Activation of C(sp2)–H Bonds DOI

Minjing Yuan,

Zikang Li,

Wenli Shang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16663 - 16678

Published: Nov. 1, 2024

A novel and straightforward method for the iron-catalyzed regioselective cross-dehydrogenative coupling of para-quinone methides (p-QMs) with formamides has been developed, facilitated by in situ activation C(sp2)–H bonds formyl alkenyl substituents via a radical strategy. This does not require preactivation substrates, it can accommodate wide range p-QMs under optimized reaction conditions, resulting formation expected C-7 acetamides-functionalized moderate to good yields. The control experiments revealed that follows fundamental equation second-order kinetics. Additionally, an exploration Hammett effect was undertaken elucidate impact reaction. In combination DFT calculation, plausible mechanism proposed through meticulously controlled experiments.

Language: Английский

Citations

0
Transition metal-free Csp3-Csp3 bond-forming reactions of N-tosylaziridines and gem-diborylalkanes DOI Creative Commons

Pu-Zhang Zi,

Quan-Hong Zhao,

Zhan-Cai Ma

et al.

Green Synthesis and Catalysis, Journal Year: 2023, Volume and Issue: 5(4), P. 329 - 333

Published: July 26, 2023

The incorporation of additional Csp3 atoms into candidate drugs may enhance their pharmacological properties. Nevertheless, it remains challenging to construct desired Csp3-Csp3 bonds efficiently and practically. present article reports a novel bond-forming reaction 2-aryl/alkyl substituted aziridines with gem-diborylalkanes under tranisiton metal free conditions. A wide range γ-gem-diboronate esters amines can be accessed in good yield regioselectivity. results demonstrated that various could react the presence LiTMP as base within 15 min at ambient temperature.

Language: Английский

Citations

0
Selective Oxidative Methyl C–H Functionalization of Butylated Hydroxytoluene toward Arylimines/N-Heterocycles DOI
Jianyu Dong,

Shaofeng Wu,

Furong Geng

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(20), P. 14649 - 14658

Published: Oct. 10, 2023

A metal-free and selective oxidative methyl C-H functionalization of BHT with aniline compounds has been developed. This innovative method enables the facile efficient synthesis a diverse array BHT-functionalized N-containing skeletons, including arylamines, benzoxazoles, benzothiazoles, benzimidazoles, quinazolines, quinazolinones, all which are challenging to access. The control experiment involving TEMP18O suggests that radical adduct TEMPO benzyl may serve as an intermediate.

Language: Английский

Citations

0