Synthesis of Benzofuran Derivatives through Cascade Radical Cyclization/Intermolecular Coupling of 2-Azaallyls
By: Deng, GG (Deng, Guogang)  ; Li, MY (Li, Minyan) ; Yu, KL (Yu, Kaili) ; Liu, CX (Liu, Chunxiang) ; Liu, ZF (Liu, Zhengfen) ; Duan, SZ (Duan, Shengzu) ; Chen, W (Chen, Wen) ; Yang, XD (Yang, Xiaodong) ; Zhang, HB (Zhang, Hongbin) ; Walsh, PJ (Walsh, Patrick J.)
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Published: FEB 25 2019
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.
Author Keywords: azaallyl anions; benzofurylethylamine; cascade reactions; radical coupling; radical cyclization
KeyWords Plus: SUPER-ELECTRON-DONORS; CYCLIZATION
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.
[ 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
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