Development and Scale-Up of a Novel Photochemical C-N Oxidative Coupling

被引：14

作者：

Robinson, Alan ^{[1
]}

Dieckmann, Michael ^{[1
]}

Krieger, Jean-Philippe ^{[1
]}

Vent-Schmidt, Thomas ^{[1
]}

Marantelli, Dominique ^{[1
]}

Kohlbrenner, Ralf ^{[1
]}

Gribkov, Denis ^{[1
]}

Simon, Levente L. ^{[1
]}

Austrup, David ^{[1
]}

Rod, Alexandre ^{[2
]}

Bochet, Christian G. ^{[2
]}

机构：

[1] Syngenta Grp, CH-4333 Munchwilen, Switzerland

[2] Univ Fribourg, Dept Chem, CH-1700 Fribourg, Switzerland

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2021年 / 25卷 / 10期

关键词：

C-N coupling; photochemistry; scale-up; pyridazinone; agrochemistry; PHOTOREDOX CATALYSIS; SINGLET OXYGEN; NAPHTHALENE; REACTOR; EXCIPLEX; YIELD; BATCH; UV;

D O I：

10.1021/acs.oprd.1c00244

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A visible light promoted C-N-coupling of a functionalized pyridazinone with veratrole was developed to forge the central C-N bond of an agrochemical intermediate. Dosing aqueous NaOCl and 4% O-2 in N-2 under blue light irradiation (460 nm) was key to promote the desired transformation while generating benign wastes. Mechanistic studies suggest the formation of a N-chloro species that undergoes selective coupling via a radical pathway induced by the combination of light and oxygen. Further development led to an optimized semi-batch process, which was successfully scaled up to an initial 20 L and then 1.2 m(3).

引用

页码：2205 / 2220

页数：16

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