Fe-catalyzed three-component dicarbofunctionalization of unactivated alkenes with alkyl halides and Grignard reagents,Chemical Science

当前位置： X-MOL 学术 › Chem. Sci. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Fe-catalyzed three-component dicarbofunctionalization of unactivated alkenes with alkyl halides and Grignard reagents
Chemical Science ( IF 7.6 ) Pub Date : 2020-07-24 , DOI: 10.1039/d0sc02127j
Lei Liu ₁ , Wes Lee ₁ , Cassandra R Youshaw ₁ , Mingbin Yuan ₁ , Michael B Geherty ₁ , Peter Y Zavalij ₁ , Osvaldo Gutierrez ₁

Affiliation

A highly chemoselective iron-catalyzed three-component dicarbofunctionalization of unactivated olefins with alkyl halides (iodides and bromides) and sp²-hybridized Grignard reagents is reported. The reaction operates under fast turnover frequency and tolerates a diverse range of sp²-hybridized nucleophiles (electron-rich and electron-deficient (hetero)aryl and alkenyl Grignard reagents), alkyl halides (tertiary alkyl iodides/bromides and perfluorinated bromides), and unactivated olefins bearing diverse functional groups including tethered alkenes, ethers, protected alcohols, aldehydes, and amines to yield the desired 1,2-alkylarylated products with high regiocontrol. Further, we demonstrate that this protocol is amenable for the synthesis of new (hetero)carbocycles including tetrahydrofurans and pyrrolidines via a three-component radical cascade cyclization/arylation that forges three new C–C bonds.

中文翻译：

Fe 催化卤代烷和格氏试剂对未活化烯烃的三组分二碳官能化

报道了一种高度化学选择性的铁催化的未活化烯烃与烷基卤化物（碘化物和溴化物）和 sp ²杂化格氏试剂的三组分二碳官能化反应。该反应在快速周转频率下进行，可耐受多种 sp ²杂化亲核试剂（富电子和缺电子（杂）芳基和烯基格氏试剂）、烷基卤化物（叔烷基碘化物/溴化物和全氟化溴化物），以及带有多种官能团的未活化烯烃，包括束缚烯烃、醚、受保护的醇、醛和胺，可产生具有高区域控制性的所需 1,2-烷基芳基化产物。此外，我们证明该方案适合通过三组分自由基级联环化/芳基化合成新的（杂）碳环，包括四氢呋喃和吡咯烷，形成三个新的 C-C 键。

更新日期：2020-08-12

点击分享查看原文

点击收藏

公开下载

阅读更多本刊最新论文本刊介绍/投稿指南11