Synthesis of Benzofuran Derivatives through Cascade Radical Cyclization/Intermolecular Coupling of 2-Azaallyls
By: Deng, GG (Deng, Guogang) [1] ; Li, MY (Li, Minyan)[2] ; Yu, KL (Yu, Kaili)[1] ; Liu, CX (Liu, Chunxiang)[1] ; Liu, ZF (Liu, Zhengfen)[1] ; Duan, SZ (Duan, Shengzu)[1] ; Chen, W (Chen, Wen)[1] ; Yang, XD (Yang, Xiaodong)[1] ; Zhang, HB (Zhang, Hongbin)[1] ; Walsh, PJ (Walsh, Patrick J.)[2]
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume: 58
Issue: 9
Pages: 2826-2830
DOI: 10.1002/anie.201812369
Published: FEB 25 2019
Document Type:Article
Abstract
Benzofurans are among the most popular structural units in bioactive natural products, however, the synthesis of such structures by radical cyclization cascade reactions is rare. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade mechanism. Single-electron transfer (SET) from 2-azaallyl anions to 2-iodo aryl allenyl ethers initiates a radical cyclization that is followed by intermolecular radical-radical coupling. This expedient approach enables the synthesis of a range of polycyclic benzofurans that would otherwise be difficult to prepare.
Keywords
Author Keywords: azaallyl anions; benzofurylethylamine; cascade reactions; radical coupling; radical cyclization
KeyWords Plus: SUPER-ELECTRON-DONORS; CYCLIZATION
Author Information
Reprint Address: Yang, XD; Zhang, HB (reprint author)
Yunnan Univ, Key Lab Med Chem Nat Resources, State Key Lab Conservat & Utilizat Bioresources Y, Minist Educ & Yunnan Prov,Sch Chem Sci & Technol, Kunming 650091, Yunnan, Peoples R China.
Reprint Address: Walsh, PJ (reprint author)
Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, 231 South 34th St, Philadelphia, PA 19104 USA.
Addresses:
[ 1 ] Yunnan Univ, Key Lab Med Chem Nat Resources, State Key Lab Conservat & Utilizat Bioresources Y, Minist Educ & Yunnan Prov,Sch Chem Sci & Technol, Kunming 650091, Yunnan, Peoples R China
[ 2 ] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, 231 South 34th St, Philadelphia, PA 19104 USA
全文链接：https://www.onlinelibrary.wiley.com/doi/full/10.1002/anie.201812369
