I2-Induced Metal-Free C(sp2)–H Functionalization of Indoles via One-Pot and Two-Step Reaction with 1-(2-Hydroxyphenyl)-propargyl Alcohols: Access to 3-(Benzofuran-3-yl)-1H-indoles DOI

Yang Zhu,

Guisheng Deng

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

Published: April 3, 2025

The I2-catalyzed reaction of 1-(2-hydroxyphenyl)-propargyl alcohols with indoles and subsequent treatment K2CO3 provided (benzofuran-3-yl)-1H-indoles in good to excellent yields high regioselectivity. This one-pot two-step strategy proved be suitable for a wide range substrates except aliphatic alkynyl as well the bearing N-protected groups such Ts group possessing strong electron-withdrawing feature. procedure involved cross-coupling construction benzofuran framework via 5-exo-dig cyclization.

Language: Английский

Oxo-Sulfonylation of 1,7-Enynes via a Multicomponent Oxidative Radical Polar Crossover Approach DOI
Pooja Yadav,

P. Sinha,

Purushothaman Gopinath

et al.

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

Published: Jan. 10, 2025

Diastereoselective synthesis of trans-3,4-difunctionalized tetrahydroquinoline and chromane derivatives via the oxo-sulfonylation 1,7-enynes is demonstrated. The reaction involves a three-component oxidative radical polar crossover (ORPC) approach wherein vinyl carbocation intermediate undergoes nucleophilic substitution to afford corresponding keto functional group. Deprotection N-Ts group, gram-scale synthesis, other synthetic applications were illustrated. Control experiments mechanistic studies show that water acts as nucleophile in this reaction.

Language: Английский

Citations

1
I2-Induced Metal-Free C(sp2)–H Functionalization of Indoles via One-Pot and Two-Step Reaction with 1-(2-Hydroxyphenyl)-propargyl Alcohols: Access to 3-(Benzofuran-3-yl)-1H-indoles DOI

Yang Zhu,

Guisheng Deng

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

Published: April 3, 2025

The I2-catalyzed reaction of 1-(2-hydroxyphenyl)-propargyl alcohols with indoles and subsequent treatment K2CO3 provided (benzofuran-3-yl)-1H-indoles in good to excellent yields high regioselectivity. This one-pot two-step strategy proved be suitable for a wide range substrates except aliphatic alkynyl as well the bearing N-protected groups such Ts group possessing strong electron-withdrawing feature. procedure involved cross-coupling construction benzofuran framework via 5-exo-dig cyclization.

Language: Английский

Citations

0