Fe-catalyzed three-component dicarbofunctionalization of unactivated alkenes with alkyl halides and Grignard reagents.
Fe-catalyzed three-component dicarbofunctionalization of unactivated alkenes with alkyl halides and Grignard reagents.
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DOI：
10.1039/d0sc02127j
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发表时间：
2020-07-24
期刊：
影响因子：
8.4
通讯作者：
Gutierrez O
中科院分区：
文献类型：
--
作者：
Liu L;Lee W;Youshaw CR;Yuan M;Geherty MB;Zavalij PY;Gutierrez O
报道了一种高化学选择性的铁催化的未活化烯烃与卤代烷（碘和溴）和sp2杂化格氏试剂的三组分双碳官能化反应。该反应在快速转换频率下进行，并耐受多种sp2-杂交亲核试剂（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/溴和全氟化溴），和带有不同官能团的未活化烯烃，包括系链烯烃、醚、受保护的醇、醛和胺，得到所需的1，具有高区域控制的2-烷基化产物。此外，我们证明，该协议是适合于新的（杂）碳环，包括四氢呋喃和吡咯烷通过三组分自由基级联环化/芳基化，锻造三个新的C-C键的合成。报道了一种高选择性的铁催化未活化烯烃与卤代烷和sp2杂化格氏试剂的三组分双碳官能化反应。
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. A highly selective iron-catalyzed three-component dicarbofunctionalization of unactivated alkenes with alkyl halides and sp2-hybridized Grignard reagents is reported.
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影响因子：
15
作者：
Lo JC;Kim D;Pan CM;Edwards JT;Yabe Y;Gui J;Qin T;Gutiérrez S;Giacoboni J;Smith MW;Holland PL;Baran PS
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