Electroreductive Remote Benzylic C(sp3)-H Arylation of Aliphatic Ethers Using Cyanoarenes for the Synthesis of α-(Hetero)aryl Ethers

Liang Zeng; Hua-Zhan Ren; Gui-Fen Lv; Xuan-Hui Ouyang; De-Liang He; Jin-Heng Li

doi:10.1021/acs.orglett.4c00615

Electroreductive Remote Benzylic C(sp³)-H Arylation of Aliphatic Ethers Using Cyanoarenes for the Synthesis of α-(Hetero)aryl Ethers

Org Lett. 2024 Mar 29;26(12):2440-2444. doi: 10.1021/acs.orglett.4c00615. Epub 2024 Mar 19.

Authors

Liang Zeng^{1

2

3}, Hua-Zhan Ren², Gui-Fen Lv¹, Xuan-Hui Ouyang¹, De-Liang He³, Jin-Heng Li^{1

2

3

4}

Affiliations

¹ Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China.
² State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China.
³ State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, China.
⁴ State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.

PMID: 38502576
DOI: 10.1021/acs.orglett.4c00615

Abstract

An iodoarene-driven electroreductive remote C(sp³)-H arylation of unsymmetrical 1-(o-iodoaryl)alkyl ethers with cyanoarenes for the site selective synthesis of α-(hetero)aryl ethers is developed. With the introduction of cyanoarenes as both aryl sources and electron transfer mediators, this method includes an iodoarene-driven strategy to enable the regiocontrollable formation of two new bonds, one C(sp²)-H bond, and one C(sp²)-C(sp³) bond, in a single reaction step through the sequence of halogen atom transfer (XAT), hydrogen atom transfer (HAT), radical-radical coupling, and decyanation.