Integrated continuous-flow/batch protocol for ortho-selective alkynylation of (hetero)aryl tosylates

被引：0

作者：

Ju, Eun-Hae ^{[1
]}

Lee, Min-Jung ^{[1
]}

Song, Jiwoo ^{[1
]}

Kwon, Yong-Ju ^{[1
,2
]}

Kim, Won-Suk ^{[1
,2
]}

机构：

[1] Ewha Womans Univ, Dept Chem & Nanosci, Seoul, South Korea

[2] Ewha Womans Univ, Dept Chem & Nanosci, Seoul 03760, South Korea

来源：

BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2023年 / 44卷 / 09期

基金：

新加坡国家研究基金会;

关键词：

alkynylation; flow chemistry; Negishi coupling; regioselectivity; zincation; ALKYNYLZINC; BENZOFURANS; AILANTHOIDOL;

D O I：

10.1002/bkcs.12717

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The ortho-selective alkynylation of polyhalo-substituted (hetero)aryl tosylates was investigated using an integrated continuous-flow/batch protocol. Without the elimination of the tosyloxy group, the regioselective ortho-metalation of the (hetero)aryl tosylates employing n-BuLi and ZnCl2 was successfully achieved in continuous-flow chemistry within 10.92 s (residence time). The Pd-catalyzed Negishi alkynylations of various iodoethynyl (hetero)arenes and the resulting arylzinc species proceeded at room temperature in yields ranging from 51% to 95%. Finally, the synthetic utility of this strategy was validated by the synthesis of benzofuran and pyridofuran derivatives.

引用

页码：772 / 776

页数：5