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A Sustainable 1-Pot, 3-Step Synthesis of Boscalid Using Part per Million Level Pd Catalysis in Water
Organic Process Research & Development ( IF 3.4 ) Pub Date : 2019-12-13 , DOI: 10.1021/acs.oprd.9b00455
Balaram S. Takale 1 , Ruchita R. Thakore 1 , Rushil Mallarapu 1, 2 , Fabrice Gallou 3 , Bruce H. Lipshutz 1
Affiliation  

Boscalid is an active ingredient in several fungicides marketed by the BASF. Literature approaches use multipot processes, organic solvents, and unsustainable levels of palladium catalysis. Herein is disclosed a 1-pot, 3-step route using nanomicelles in water as the reaction medium and a very low loading (700 ppm or 0.07 mol %) of costly and endangered Pd. The sequence developed involves an initial Suzuki–Miyaura cross-coupling, the product from which is not isolated. The second step relies on a carbonyl iron powder (CIP) reduction of the aryl nitro group, followed by the third and final step involving an acylation with the required 2-chloronicotinyl chloride. The overall isolated yield for these three steps is 83%.

中文翻译:

水中百万分之几的Pd催化可持续地进行一锅三步合成Boscalid

巴斯卡德(Boscalid)是巴斯夫(BASF)销售的几种杀菌剂中的活性成分。文献方法使用多锅法,有机溶剂和不可持续的钯催化水平。本文公开了一种使用在水中的纳米胶束作为反应介质以及非常低的负载量(700ppm或0.07mol%)的昂贵且濒临灭绝的Pd的一锅三步路线。所开发的序列涉及最初的Suzuki-Miyaura交叉偶联,尚未分离出产物。第二步依赖于芳基硝基的羰基铁粉(CIP)还原,随后的第三步也是最后一步,涉及用所需的2-氯烟酰氯进行酰化。这三个步骤的总分离产率为83%。
更新日期:2019-12-13
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