Sutter Patrick J, Kang Guowei, Vellalath Sreekumar, Romo Daniel
Department of Chemistry and Biochemistry, Baylor University Waco 76798 Texas USA
Department of Chemistry, The Scripps Research Institute 10550 N. Torrey Pines Road La Jolla 92037 California USA.
RSC Adv. 2023 Jan 24;13(6):3468-3473. doi: 10.1039/d2ra07715a.
Zinc-mediated carboxylation of allylic halides under flow conditions delivered β,γ-unsaturated carboxylic acids and subsequent bromolactonization provides a streamlined process for the synthesis of γ-bromo-β-lactones. The described process further demonstrates the utility of organozinc reagents prepared by passage of allylic halides through a metallic zinc column integrated into a flow process. Use of a tube-in-tube reactor for efficient CO introduction led to improvements in conversion compared to a batch process and improved overall yields of β-lactones. The described flow process was also applied to propargylic bromides for the synthesis of allenic and propargylic acids.
在流动条件下，锌介导的烯丙基卤化物的羧化反应生成β,γ-不饱和羧酸，随后的溴内酯化反应为γ-溴-β-内酯的合成提供了一种简化的方法。所描述的过程进一步证明了通过将烯丙基卤化物通过集成到流动过程中的金属锌柱制备的有机锌试剂的实用性。与间歇过程相比，使用套管式反应器进行高效的一氧化碳引入提高了转化率，并提高了β-内酯的总产率。所描述的流动过程也应用于炔丙基溴化物，用于合成联烯酸和炔丙基酸。
