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

Visible-light induced direct C(sp3)–H functionalization: recent advances and future prospects DOI
Jia‐Lin Tu, Yining Zhu, Pengcheng Li

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5278 - 5305

Published: Jan. 1, 2024

This review summarizes the latest methodological advances in photocatalytic C(sp 3 )–H functionalization, with a particular emphasis on formation of C–P, C–B, C–S bonds, etc ., and some prominent efforts asymmetric C–H functionalization.

Language: Английский

Citations

15
Acyl radicals generated from aldehydes with NHPI as electrocatalyst: aldehydes and alcohols as carbon-centered radical precursors DOI Creative Commons
Rodrigo G. Enríquez, Juan S. Dato-Santiago, Roberto del Río‐Rodríguez

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4842 - 4848

Published: Jan. 1, 2024

We describe how N -hydroxyphthalimide (NHPI) promotes hydrogen atom transfer from aldehydes under electrochemical conditions. NHPI plays a multifunctional role, enabling the consideration of or alcohols as sp 3 -carbon centered radicals.

Language: Английский

Citations

2
Electro-promoted radical-radical cross-coupling reaction to synthesize sulfonamides DOI
Hang Gong,

Hongmei Fu,

Chao Lü

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 168, P. 134315 - 134315

Published: Oct. 20, 2024

Language: Английский

Citations

0
Direct C-H functionalisation of azoles via Minisci reactions DOI Creative Commons
Ai‐Lan Lee,

David T. Mooney,

Heather McKee

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

This review gives an overview of the C–H functionalisation azoles via Minisci-type reactions, highlighting recent progress, existing limitations and potential areas for growth.

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