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Continuous-flow photo-induced decarboxylative annulative access to fused imidazole derivatives via a microreactor containing immobilized ruthenium
Green Chemistry ( IF 9.8 ) Pub Date : 2020/02/06 , DOI: 10.1039/c9gc03496j
Praveen Reddy Adiyala 1, 2, 3, 4 , Seungwook Jang 5, 6, 7, 8, 9 , Niraj K. Vishwakarma 4, 10, 11, 12 , Yoon-Ho Hwang 5, 6, 7, 8, 9 , Dong-Pyo Kim 5, 6, 7, 8, 9
Affiliation  

Visible-light-driven continuous-flow decarboxylative annulation was achieved and used along with a microreactor containing immobilized ruthenium catalyst to construct valuable fused imidazole derivatives with high yields under an open atmosphere. Notably, this chemistry included the use of L-proline and α-azidochalcone as precursors of an α-amino radical and 2H-azirine via photo-induced decarboxylation and denitrogenation, respectively, to give the annulated imidazole derivatives as a result of the formation of two new C–N bonds. Moreover the novel, environmentally benign and efficient continuous-flow protocol was further improved by carrying out the reaction in a polydimethylsiloxane (PDMS) microreactor with immobilized Ru3+ under fluorescent or white LED light, enabling excellent yields (70–94%) at a reaction time (2 min) significantly shorter than that (16 h) of the batch protocol.

中文翻译:

通过含固定化钌的微反应器连续流光诱导的脱羧环化反应,获得稠合的咪唑衍生物

实现了可见光驱动的连续流脱羧环化反应,并将其与包含固定化钌催化剂的微反应器一起用于在开放气氛下以高收率构建有价值的稠合咪唑衍生物。值得注意的是,该化学方法包括通过光诱导的脱羧和脱氮作用,分别使用L-脯氨酸和α-azidochalcone作为α-氨基自由基和2 H -azirine的前体,从而形成环化的咪唑衍生物。两个新的C–N债券。此外,通过在固定有Ru 3+的聚二甲基硅氧烷(PDMS)微反应器中进行反应,进一步改善了新颖,环保,有效的连续流方案 在荧光灯或白光LED灯下,反应时间(2分钟)比批处理方案的反应时间(16小时)短,因此可获得出色的收率(70-94%)。
更新日期:2020-03-09
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