An Organometallic Umpolung Approach for Iron‐Mediated Propargylic C–H Etherification DOI Creative Commons
Yue Xia, Jin Zhu,

Austin C. Durham

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 27, 2024

Abstract Propargylic ethers serve as useful intermediates for the synthesis of a variety complex targets. However, propargylic substitution prefunctionalized alkyne starting materials remains dominant method propargyl ethers, while direct etherification simple alkynes via C−H functionalization largely underreported. Herein, we report an organometallic umpolung approach iron‐mediated etherification. A telescopic protocol deprotonation followed by mild oxidative coupling with alcohols enabled use or functionalized expedient excellent functional group compatibility, chemoselectivity and regioselectivity.

Language: Английский

Hydrogen Bond-Mediated Transition Metal-Free Alcoholysis of Primary Amides to Access Esters DOI

Yingguo Ban,

Enhua Wang,

Ke Ren

et al.

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

Published: Jan. 24, 2025

An efficient hydrogen bond-mediated alcoholysis of primary amides was disclosed using diethyl phosphonate (DEP) as a catalyst. In this process, wide range and alcohols were tested smoothly transformed to corresponding esters in moderate good yields. This novel strategy features transition metal-free, broad substrate scope one-pot pathway. addition, the reaction showed highly chemoselective o/alcoholic o-acylation mercapto/phenolic alcohols.

Language: Английский

Citations

0
The influence of acid additive on linear and branch selectivity in the C−H alkylation of the N-pyridinecarbonyl protected 2-methylbenzylamine with 1-heptene catalyzed by Rh2(OAc)4: a theoretical investigation DOI

Lingli Han,

Fei Guan,

Zifan Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

The role of an acid additive and the origins reaction are clarified through our calculations.

Language: Английский

Citations

0
An Organometallic Umpolung Approach for Iron‐Mediated Propargylic C–H Etherification DOI Creative Commons
Yue Xia, Jin Zhu,

Austin C. Durham

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 27, 2024

Abstract Propargylic ethers serve as useful intermediates for the synthesis of a variety complex targets. However, propargylic substitution prefunctionalized alkyne starting materials remains dominant method propargyl ethers, while direct etherification simple alkynes via C−H functionalization largely underreported. Herein, we report an organometallic umpolung approach iron‐mediated etherification. A telescopic protocol deprotonation followed by mild oxidative coupling with alcohols enabled use or functionalized expedient excellent functional group compatibility, chemoselectivity and regioselectivity.

Language: Английский

Citations

1
An Organometallic Umpolung Approach for Iron‐Mediated Propargylic C–H Etherification DOI Creative Commons
Yue Xia, Jin Zhu,

Austin C. Durham

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 27, 2024

Abstract Propargylic ethers serve as useful intermediates for the synthesis of a variety complex targets. However, propargylic substitution prefunctionalized alkyne starting materials remains dominant method propargyl ethers, while direct etherification simple alkynes via C−H functionalization largely underreported. Herein, we report an organometallic umpolung approach iron‐mediated etherification. A telescopic protocol deprotonation followed by mild oxidative coupling with alcohols enabled use or functionalized expedient excellent functional group compatibility, chemoselectivity and regioselectivity.

Language: Английский

Citations

0