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

Pd-catalyzed 5-exo-dig cyclization/etherification cascade of N-propargyl arylamines for the synthesis of polysubstituted furans DOI

Mengru Li,

Meng-Yao Zheng,

Dong‐Chao Wang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(60), P. 7721 - 7724

Published: Jan. 1, 2024

A method for the synthesis of furans bearing indoline skeletons was developed

Language: Английский

Citations

0
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