Two-Step Continuous-Flow Synthesis of Fungicide Metalaxyl through Catalytic C-N Bond-Formation Processes

被引：5

作者：

Ishitani, Haruro ^{[1
]}

Yu, Zhibo ^{[2
]}

Ichitsuka, Tomohiro ^{[3
,4
]}

Koumura, Nagatoshi ^{[4
]}

Onozawa, Shun-ya ^{[4
]}

Sato, Kazuhiko ^{[4
]}

Kobayashi, Shu ^{[1
,2
,4
]}

机构：

[1] Univ Tokyo, Grad Sch Sci, Green & Sustainable Chem Social Cooperat Lab, Bunkyo Ku, Tokyo 1330033, Japan

[2] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

[3] Natl Inst Adv Ind Sci & Technol, Res Inst Chem Proc Technol, Nigatake 4-2-1, Sendai, Miyagi 9838551, Japan

[4] Natl Inst Adv Ind Sci & Technol, Interdisciplinary Res Ctr Catalyt Chem, Cent 5,Higashi 1-1-1, Tsukuba, Ibaraki 3058565, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 01期

关键词：

sequential continuous-flow; reductive alkylation; heterogeneous catalyst; amidation; metalaxyl; REDUCTIVE AMINATION; GREEN; ALKYLATION;

D O I：

10.1002/adsc.202100898

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Metalaxyl, an acylalanine fungicide, was synthesized through catalytic continuous sequential-flow reactions. Commonly used syntheses of this compound use batch systems and suffer from problems such as coproduction of halogen-containing by-products derived from acyl and alkyl halides in the substitution reactions of 2,6-dimethylaniline. To minimize waste and enhance efficiency, a halide-free approach including two continuous-flow catalytic processes, heterogeneous Pt-catalyzed reductive alkylation and homogeneous acid-catalyzed amidation with an acid anhydride, was developed. Systematic examination of the two reactions in flow mode enabled a high-yielding, two-step sequential continuous-flow process to be achieved.

引用

页码：18 / 23

页数：6

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